I started this out as a note but it is becoming a full post now. A way to express my insecurities when I SHOULD know better.

I know starting with Pinterest is NOT how I get inspired.

I know I am not Influencer A who does quiet luxury SO well and I know I am not influencer B who is a QUEEN with accessories.

I know I will feel my best if I am feeling comfortable.

And yet, I am falling into all of these traps as I plan my outfits for NYFW.

Hell, I KNOW outfit planning does not does not work for me yet here we are!

You see, how I get dressed is very simple. I go with the vibe I am feeling that day, sometimes start with a simple theme (jeans!), other times not..just start with a favorite piece..and build up from there. Something feels too masculine, add femme. Something feels too pretty, add weird. So on and so forth. Till I reach a place where I feel good, I feel like me.

I have extensive experience doing this while traveling too. I know how to pack a capsule with friction, so I have all the elements possible to get dressed based on vibe every single day.

I know all this, but NYFW is HIGH pressure. Even though I know no one else gives a fuck. But y’all, the minute I think I should just do this as I always do, I am having a wave of panic come up.

I am going to 4 events (YAY!) where there will be actual photographers. Will people be expecting me to show up as a more elevated version of me? Is it wasting opportunity if I don’t? Waste which opportunity? I don’t know to be honest.

Worth noting I did this thing last year too, the whole NYFW thing. BUT, I was not this distressed over it last year. Why? Maybe coz I was not invited to any events as a ‘creator’ the way I am this year.

This year, I made the mistake of searching for NYFW on Pinterest and the way it has imposter syndrome hit me. Now, thank goodness I am not someone and have never been someone who worries too much about my age, weight, height, size, hair color, skin color etc not being like the cool girls.

BUT, their outfits! I do not accessorize like THAT. I do not wear heels that high. My outfits are not ‘special enough’ like these people to ‘make it’. Make it where? I also do not know.

So I have been trying on fits I have been hating this entire weekend. Now do note I played around with some outfits earlier this month and that went just fine. But what is it this time? Maybe that I am not starting from my closet. Maybe that I am not starting from ME. I am starting outwards in.

To be like the Pinterest girls.

To be ‘worthy’ of being invited to these events.

And honestly, to be more than what I would be if I did not try hard enough. I am relentless about growth, which serves me well..but also is just high pressure.

And I am failing. I continue to fail with every single outfit.

This has also left me wondering if I am just hormonal. What worked last month that is not working now?

So I am going to give up. For now. I have a work trip next week. I excitedly put together a packing capsule for it (bay area executive summit) that I love. Phew, this is in my wheelhouse I got THIS at least.

When I come back, I will be re-energized. I will be less hormonal. I will be less creatively blocked. And I will start AGAIN from ME. Inwards out.

I know I can do it, because I always do. Re-anchor in the self. Selfish style, all about me, all for me. <3

Okay, that’s a wrap for this one!

If something in here made you nod, send it to the friend who would also nod. That’s genuinely all I want, along with a few more things of course:

🔁 Restack or quote the part that hit, it helps more than you’d think. Especially since I don’t do paid subscriptions, Substack won’t push this one out without your help

💖 Like or comment if you have feelings (I will read every single one!)

🔔 Not subscribed yet? Subscribe, friend!

Find me on Instagram @astahearts for more outfit overthink-ery!

I was gonna title this one ‘the urge to purge’ then I remembered the 2000s and the skinnymania hell we are going through AGAIN and decided to not choose chaos. Great start to this post, we digress already! Back to the topic at hand: This one is about all of us who ‘create content’ (ew) here or IG or anywhere being so so intentional about the audience we are attracting and the community we are creating. But also maybe, this one is about a lot more than content creation, keep reading I promise I have a point here.

So I went from 200 something followers on IG to…(checking) 164K in a little bit more than one year. A lot of these numbers come from bursts of viral posts. It’s like you get about 100 followers per post…then there’s a viral one that brings in tens of thousands…and then back to 100ish per post. The issue is, some of these viral posts are high alignment with who I am as a person, and some are not.

This is where I introduce you to how I think about my community that I am trying to create here and on IG. It is concentric circles, something like this:

• Bullseye:

  • 35+ yr old women who love fashion

  • see personal style as a tool to show who they are

  • do not think there is only one way to do fashion right

  • are unapologetic (or at least are trying to be)

  • do not think shopping is the devil!

  • respect boundaries (their own and others’)

  • believe ambition is good for women

  • believe women deserve to make money

  • do not believe in duping others to do so

• Second circle (we drop a few attributes):

  • 35+ yr old women who love fashion

  • see personal style as a tool to show who they are

  • do not think there is only one way to do fashion right

  • are unapologetic (or at least are trying to be)

  • do not think shopping is the devil!

  • respect boundaries (their own and others’)

• Third circle (drop some more):

  • 35+ yr old women who love fashion

  • see personal style as a tool to show who they are

  • do not think there is only one way to do fashion right

  • do not think shopping is the devil!

• Fourth circle (yet broader):

  • 35+ yr old women who love fashion

  • see personal style as a tool to show who they are

  • do not think there is only one way to do fashion right

• Fifth circle (fairly open):

  • 35+ yr old women who love fashion

  • see personal style as a tool to show who they are

• Last circle (come on this is the most generic one ever)

  • 35+ yr old women who love fashion

I want the most people to be in the first 2, or at least first 3 circles. And the least amount of people in that last one. But not all my content is always only that first circle, right? Sometimes it is just a fitcheck, attracting a lot of audience that is 6th circle only. Sometimes it might even be just a quote on confidence, and then I get a bunch of very low alignment followers. They might make some sort of a venn diagram where they belive that women should be ambitious and make money, but they might not be interested in style and fashion at all!

Examples

This reel going viral likely earned me 1st and 2nd circle community:

However, this one going mega viral is probably a lot of last circle community:

While this one is somewhere in the middle:

Why does any of this matter?

There’s a concept called Audience Capture in content creation. It is natural for us to double down on ‘what’s working’. But what works isn’t universal or random. If a majority of my community is 6th circle, then what will work is ANY fashion content. Including things that I do not myself believe in (like trends).

A natural thing that happens is we forget who we are, what we stand for, and start performing for the algorithm. Ok, let’s do 5 more videos struggling with Kellies and Birkins because that one REALLY blew up. Let’s do more preachy quotes about confidence, since that seems to hit a chord. Let’s also throw in 5 more ways to style this tiger top because that ALWAYS hits.

And at the end of the day, your feed becomes something YOU don’t recognize or like. And any time you do stuff that is YOU, no one appreciates that anymore because that is just not your audience. You built a community that is completely out of alignment. And now you are trapped inside of it.

And why does THAT matter?

One thing I did not fully understand about creating content is how much that is a reflection of who you are, your values, your light, and your shadow. And how much it can drive your mental health, and to some extend inner compass. Or well, that is true for how I like to do stuff. I did not sit down and write my 5 content pillars and create a schedule (lol anyone who reads my stuff here probably knows that about me). I am just creating what I am thinking. SO, the logical conclusion is what I am creating must also be driving what I am thinking next. And what a shame it would be if I let audience capture dilute my thinking, my values, my approach to life. Oof!

And hence, the purge post

At this point, I have a very good understanding of what will make people unfollow/unsubscribe. They are all the things that live on the peripheries of the circles I describe above. I have made it a regular practice to make posts highlighting those factors every time after a viral post. With the sole purpose of driving people to opt out of this ride if it’s not for them. Here is my list:

• People who are anti shopping (I get this, trust me I do. But I am not anti shopping and if this is gonna piss you off, better you find out sooner rather than later). The purge post.

• People who are anti AI (AI is very dangerous, but I truly believe if done right, will be net positive for society. Hence, I do what I do. In my experience most people who are vehemently anti AI don’t even begin to understand it, and are anti ‘creation with AI’. I get that, I respect it, but AI is much more than creating content. For folks who don’t care about that distinction and given my job, my life this one is a good reason to opt out. The purge post.

• People who hate Google. Weird flex to be on a Meta platform and send me an abhorrent DM about my job, but you do you. This one I also add to my welcome message so people can opt out right away. The purge post.

• People who are super anti synthetic fibers. I get it, if someone else wearing synthetics REALLY bothers you, you won’t like it here anyway. The purge post.

• People who hate Tibi (lol but this is an active category especially here on Substack). So I had someone who followed me, then I found out they were complaining about me wearing Tibi all the time. Then I blocked them. They found me on a different platform to ask me why. LOL grrrlll this account is not for you if Tibi triggers you. On this one literally my entire account should be the purge post yet here we are.

• The trad-wife people. This was my biggest concern with the Kelly post going viral. There is a huge overlap in trad wives and Hermes bag owners (ew). The way I BLASTED my anti male gaze agenda after every time I got a wave of followers from that post. Please please unfollow this account isn’t what you think it is. The purge post.

So the point of the purge posts are to get people to unfollow. Like this post you are reading. I bet some people who read this will identify with one of the buckets. And unfollow, and that is great. Win-win! Sure, my numbers go down, but my community gets stronger. I know we often complain about people unfollowing/unsubscribing after a post, but oh boy if you were yourself in that post, what a relief to severe bonds where they were weak or artificial anyway, no? And the other more important point of the purge posts is reaffirming for yourself what you stand for. A reminder before you let this people pleasing veer you way off course.

And this is where real life comes in

How many times PER DAY do we perform to be liked, accepted? I always say social belonging is a core human need, but what is better? To distort yourself into a pretzel to be liked by someone you might not even like in the first place? Or be yourself SO THAT your people can find you? People pleasing tendencies are natural and common for women. Natural people we actually, literally have many, many threats all through our lives. The belief that being liked will keep us safe (and successful) is grounded in reality. At the same time, at some point this is what holds us back.

I have seen this first hand in leadership. People pleasing gets someone to a good, high level management role. And then blocks them from reaching the executive level. Because they might call you a bitch, but they sure aren’t making someone an executive if they can’t hold and stand behind a contrary opinion.

So if you are a content creator, I invite you to think about IF audience capture is driving your content creation. And how that might show up in your real life.

And if you’re not a content creator, just think about this in your real life. How much of what you do is YOU, and how much is to please the circle you have accidentally created for yourself.

For me, maybe that’s what this whole ridiculous internet experiment is really about anyway. Every time I let go of the people who only love me for a single reel or a single viral outfit, I am practicing for real life. I am teaching myself that being slightly misunderstood by strangers is a small price to pay for actually recognizing the person staring back at me in the mirror—and on MY feed.

Let’s just be US. Let them unfollow. Our people are still going to find us.

Okay, that’s a wrap for this one!

If something in here made you nod, send it to the friend who would also nod. That’s genuinely all I want, along with a few more things of course:

🔁 Restack or quote the part that hit, it helps more than you’d think. Especially since I don’t do paid subscriptions, Substack won’t push this one out without your help

💖 Like or comment if you have feelings (I will read every single one!)

🔔 Not subscribed yet? Subscribe, friend!

Find me on Instagram @astahearts for more outfit overthink-ery!

If I had a nickel for every time I got that kinda comment on IG, well idk what a nickel is so idk how much, but I would def have some sorta money by now.

I am going to address this once and for all.

But first, a story:

I did Yoga teacher training just for shits and giggles in 2020 before the great shutdown. In fact, I learn a new skill every year, always just for shits and giggles. Photography, ASL, personal finance, knitting, sewing, pole dancing, reiki practicing etc. The point is not to become an expert, but to stay in the learning mindset.

If I were a different kinda writer (teehee charming to call myself a writer but also wtf imposter syndrome) I would link you to studies, but I am not, so just trust me when I say this: a learning mindset is the best thing you can do to be a badass. When you are constantly creating new neural pathways, you are way less likely to be a perpetually annoyed, bitter bitch (no one else? that was just me? Ok nvm, in that case I did not just say that).

BUT MY POINT IS: In our class of 30, there were two people who were way quicker on the uptake than anyone else. Me, and a college student. Reader, is this because we are the only two geniuses in greater Los Angeles? Nope, it is because a college student is already in a learning mindset. We all used to be, till we stopped actively trying to acquire knowledge. And I was in the same mindset coz I actively work on that.

For anyone who has ever done dance classes, especially choreo classes, you know this. Choreo is hard to pick up at first, then as your brain gets used to HAVING to learn choreo, suddenly you are picking up new ones much faster.

OK, BUT WHAT does this have to do with getting dressed? Again, some research somewhere for sure will show you that just as you can train your brain to be in the learning mindset, you can also train your brain to be creative.

Creativity is not a magical skill that some have and others don’t.

I am a Senior Director of Design. It is my JOB to ensure people show up at their highest level of creativity. I have led teams of up to 150 people. Globally distributed. All of this to say it is literally my job to ensure not only that I am being creative, but that others can be creative.

So today I am taking all those learnings and giving you a step-by-step of how you are gonna do it.

And a rule: unless you try all of this and fail, do not tell me you are just not creative. I will also say this is not an exhaustive list. There are at least 5 more ways I can think of, so if you want a Part 2 of this post, let me know in the comments!!

Number 1: You are unlearning or at least ignoring the rules

You know when I say do not optimize for ‘flattering’? Y’all, that is NOT just a rah-rah message. This FOR REALS constrains your creativity. Because see, when I say that, people think I am advocating for everyone wearing oversized everything and the fuck not. I do not think anyone should wear the SAME of ANYTHING! What I am saying is this: if you have a rule in your head that says unless some signs of your waist are visible EVERY TIME you get dressed, the outfit is wrong. Well, that, automatically will not let you play.

We had a class called Design Methodology when I studied Industrial Design in college. The first exercise was “draw 100 ideas for a lamp inspired by a swan.” We worked on it all night, came back the next day with mayyyybe 35 to 50 ideas each. It is NOT easy to come up with 100 ideas. TILL our professor blew our minds by asking who told us to assume the entire swan had to be represented by a lamp?? What about just the neck? Just the beak? Just the wings? Just the motion? Just the color? You see what I mean? We had prescribed a rule where none existed, and that completely constrained creativity.

SO, here’s your practical activity:

• Keep a notepad next to where you get dressed. Or keep your Notes app (I mean Google Keep app, of course) handy.

• Every time you get dressed over the next week, write down all the things you believe are a must-have for your outfit. Examples: I need to make my shoulders look narrow, I cannot wear black, I must wear a belt.

• Don’t overthink, just write it down.

• Now you have a list after the week.

• Take the top thing on the list, and play when you have 15 minutes on pretend outfits that break that rule. Just do it, you don’t even need to wear the pretend fit—that’s why it is pretend. Just practice breaking the rule and see how that feels.

Number 2: Divergent thinking exercises

We actively do divergent thinking exercises at work to stay in a creative state of mind. If you have not watched my LIVEs where I demo these, first of all, friend… we need to talk. Please watch those, they are soooo fun!!

Ok, but if you haven’t, here’s a primer. Divergent thinking = an activity where you force yourself to come up with multiple solutions to the same problem. It is basically the opposite of convergent thinking (One Right Answer, like math). Creativity flourishes when you believe there are multiple ‘right’ answers.

SO here are two exercises that demo two different divergent thinking approaches:

• Take an item, style it 7 ways for 7 different real-life activities. Like this:
  

• Take an item, understand what you like about it and what you don’t like about it, then come up with divergent ways to undo or tackle what you don’t like. Like this:
  

Number 3: Stop judging others

This should be number 1, but I am making it number 3 coz I wanted you to not stop reading the post before it even began. Judgment kills creativity. We cannot be creative if we are judgmental bitches. You are judging yourself always if you are judging others. Have I convinced you already?

Now don’t get me wrong, this is easy to say, hard to do. So here I am giving you real-life examples of where I see judgment come up within myself and how I tackle it:

• Judgment: “I don’t know what everyone sees in this hugely popular creator, I do not like her style at all.”
  Reframing: If the creator is this popular, they MUST be doing something that resonates with a lot of people. And even if they were not popular, what am I judging in myself that I am having a strong reaction to them? They dress overly ornamented1. Am I judging myself when I accessorize more than minimally? (Real talk, I do!). Well shit, that is something I need to work on. There, this is about me, not them.

• Judgment: “Pairing all these bright colors together seems just visually imbalanced.”
  Reframing: TO ME. Visually imbalanced TO ME. They are not responsible for my feelings on the topic of colors. Which means… I must ALSO not be responsible for anyone’s feelings on which colors I pair together! Phew, crisis averted.

• Judgment: “People need to be prepared for the TSA line.”
  Reframing: I got nothing, people really do need to be prepared for the TSA line. OMG, is this your first day on earth??!!!

  

Number 4: Become a Pinterest pro

Are you saving outfits on Pinterest? Are you actually doing ANYTHING with said saved outfits? Well, irrespective of your answer, here’s what you are going to try:

• You are going to create a board called ‘Styling Idea Bank.’

• Search for something like “striped shirt street style2.” I STG if you start saving outfits now??!!! Resist the urge.

• You are explicitly going to look for styling details. Do you like the way the cuff is done on that one? Maybe you like the necklace layering? Or maybe the pairing of the striped shirt with a statement skirt? ONE DETAIL, only ONE DETAIL is needed for this exercise.

• Save the pin with a note for the styling detail you like.

• Do your second search. Btw, I also like <insert fav-designer name runway> for this. For example, “Dries Van Noten runway.”

• Keep saving, keep going. Bam, now you have your own idea bank in your Pinterest for styling tricks you want to try.

I do a whole IG series on this one btw, like this video:

And this one and this other one. You get the idea. And what do we do with these? Well, funny you ask coz…

Number 5: Take a photo (NO, READ THE WHOLE THING)

I know you are rolling your eyes. I know it, coz doesn’t everyone want you to do this? But ok, I am going to add another angle to it. There is a trick in real estate I learned when I was staging my condo (selling that was a BAD financial decision coz you should see the price now, but I digress). Instead of just ‘cleaning up,’ you take a photo of the room. You see in the photo where places look cluttered, then you address it. And then you take another photo. And keep going.

So, I am going to suggest an exercise for when you have play time:

• Light a candle, play some music, do whatever you need to do to create a vibe.

• Put an outfit together, maybe using one or more of the styling tricks you found on Pinterest (or my IG).

• STOP TINKERING.

• Take a photo.

• Study it, see what you want to change.

• THEN TINKER and change the thing.

• Take another photo.

• Keep going till you are done (maybe you get tired, or maybe you ran out of time).

See, low pressure? Play time, explicitly. Not, I gotta be creative in the 5 minutes I have to get ready before work.

I think y’all know this about me, but I do not plan outfits. And I get the case for outfit planning—you typically are not able to be creative under a time crunch. But here is my question: what if I said it was POSSIBLE for you to do that? Coz the thing is, it is my job to be creative on demand. So I HAVE to know how to switch it on like a faucet. It might not be your job to do this, but it sure is your desire if you have read this so far.

If so, I am not saying give up on your system that works today. BUT, supplement whatever you are doing with any of the activities above. And see what it unlocks. It is brain training, and that is good.

You know the thing about creativity? It is not selective. If you can be creative in putting an outfit together, you will be creative in solving other problems. SO I say this whole venture is worth the effort, whether you are a style overthinker or not <3

Okay, that’s a wrap for this one!

If something in here made you nod, send it to the friend who would also nod. That’s genuinely all I want, along with a few more things of course:

🔁 Restack or quote the part that hit, it helps more than you’d think. Especially since I don’t do paid subscriptions, Substack won’t push this one out without your help

💖 Like or comment if you have feelings (I will read every single one!)

🔔 Not subscribed yet? Subscribe, friend!

Find me on Instagram @astahearts for more outfit overthink-ery!

For anyone who travels for work, you know it is nowhere as glamorous as it seems to be. So I have developed coping mechanisms after about 15 years of this. The biggest one is packing for work and looking at it like a fun adventure, and using my Friction Formula for said packing.

This was a travel week for me.

• Monday: Short flight LAX to the Bay Area, meetings, dinner

• Tuesday: Meetings all day, dinner

• Wednesday: Meetings in the morning, then volunteer work, then dinner, and then drinks with a friend

• Thursday: Meetings, fly back to LA, more meetings

• Friday I was back home and boy oh boy did I have fun with my fit that day

Also, as I am trying to write this I am having the biggest internal struggle. Anyone else just cringe at the thought of journaling? I was a big fan of morning pages back in the day, and now….ughughugh…something about it just makes me cringe on the outside. It is the feeling that my life by itself, minus frameworks, minus trying to share a tip or a trick…isn’t worth writing about? I am sure my somatic healer would say that is the exact reason I SHOULD write about it.

Which also reminds me of a super interesting discussion I had with Stevie (somatic healer). You know how reels without catchy text etc. do worse on IG these days? I was REALLY feeling that and telling her how it is making me feel like I don’t have value in just….existing. I do not want to derive value from being ‘of help.’ And I usually don’t. Yet, something about content creation flies right in the face of that. Because, VALUE…is why people keep coming back. So how do you do this thing without attaching your own inherent value to how much HELP you are providing?

I don’t have answers y’all, just wondering if anyone else considers the same stuff!

So ok back to fits?

Monday

I gotta be honest, I do not feel great in casual-casual. So if I am wearing these Brancusi jeans, I am adding a striped blue shirt.

Also, WARNING, I wore this damn red jacket like literally every day this week. You know when you buy something and it is just SO YOU! This jacket is that. My…’neutral.’ Ok so anyway Monday was that. Worked perfectly for the agenda.

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Tuesday

Oh how I adore this Martine Rose graphic tee. So yall ok I usually try to tone down my style, without losing myself whenever I am in the bay area. Watch this video to see what I mean:

And I felt SO FUCKING GREAT in this fit. I mean the colors??? The silhouette??? The friction of the freakin duct tape with a trouser skirt????? Chef’s kiss, chef’s kiss, chef’s kiss.

Also, these Alohas sneakers are freaking boss. I almost did not get them coz I am not a sneaker wearer BUT it is such a good tool while I travel for work.

Wednesday (ew)

OK, ngl this was not my fav outfit. Because of what I had packed, this ended up being a casual (tee)-casual (jeans)-casual (sneakers) day. If I did not have the volunteer thing, I would have worn my Nora Lozza white sandals to offset the casual-ness. Oh well, it is what it is! It worked out perfectly for all practical purposes at least.

Thursday

Oh shit she is an outfit repeater!! It was just such a perfect airport fit, I figured why not! I really like this shirt. It has this GORGEOUS red stripe. I gotta admit I am a blue and white striped shirt ‘collector’ (sounds better than hoarder, roll with it).

This day TOOK IT OUT OF ME. Meetings, run to airport, fly back to LA, run home to do more meetings, write an entire strategy doc somewhere in there, get some bad news on a legal issue I have been dealing with (unrelated with anything here)….ooof.

I did a live try-on as soon as I was done. Husband asked me if I really needed to do it since I had a long day but ya know what, that is EXACTLY why I had to do it. Energized me greatly.

AND THEN FRIDAY, FUCK YEAH!!

Ok, so I need to write an entire post on this red fringe skirt. Girl! I bought it, returned it. Bought it again, returned it. Bought it in turquoise, returned it. Bought it in red again, ALMOST returned it. But then figured I better keep it this time so I stop burning down forests in some region somewhere on this ridiculous ordering and returning. And then I tried to style it for an art gallery opening and failed.

And then Michelle Obama wore it.

And then I FINALLY styled it for work on Friday!!!!! OMGGGGG how can an item go from ‘this is weird but I love it’ to ‘this is weird and fabulous and amazing and I love it and I want to live in it’ as soon as you unlock the ‘thing’? What is the thing I unlocked? Coming in a dedicated post.

But for now, y’all should know I also styled it AGAIN for brunch on Sunday.

Saturday

Here’s my Saturday fit. Massage. Brunch. Husband. Coz why not! Super easy, super fun. Something about colors makes my heart sing.

Is there a plan for my fits next week? Super not. Let me just make up a theme on the spot while I am at it. How about we do colors, colors, colors coz summer!! Hold on, let me start scrolling on Substack and see if I can find a theme/inspiration.

Well, here you go! I guess our theme is graphic tees for the upcoming week. Thank you, my love for the inspiration.

That’s it, y’all. See you next week in graphic tees (also should I do a post on graphic tees do we need a FRAMEWORK!!!??). I am suddenly stupid excited about this idea..ok that’s it for real now bye!

Okay, that’s a wrap for this one!

If something in here made you nod, send it to the friend who would also nod. That’s genuinely all I want, along with a few more things of course:

🔁 Restack or quote the part that hit, it helps more than you’d think. Especially since I don’t do paid subscriptions, Substack won’t push this one out without your help

💖 Like or comment if you have feelings (I will read every single one!)

🔔 Not subscribed yet? Subscribe, friend!

Find me on Instagram @astahearts for more outfit overthink-ery!

And if you like this, here’s what else I would read:

For me, it was this Tibi black mini tunic dress. A piece with an elongated collar and sculptural sleeves that I bought because it filled a gap in my closet. But the moment I put it on, I felt a little too sweet, a little too 60s/70s go-go dancer, and frankly, too young (not age-wise, just the overall vibe). My core style words are chill, modern, commanding. The dress was just not commanding enough.

Instead of letting it gather dust or immediately selling it, I decided to run a divergent thinking exercise during this LIVE to truly understand the piece, figure out what was blocking me from wearing it, and break it down through design theory.

The strategy: Unsweetening the Item

If you have a hard-to-style piece sitting in your closet, try breaking down the problem using this framework:

1. Identify the block: What is keeping you from wearing it? (For me: It felt too sweet and fitted at the waist.)

2. Identify the appeal: Why did you buy it in the first place? (For me: The gorgeous sculptural sleeves and the elongated collar.)

3. Find the opposite: If the vibe is too sweet, look for its structural opposites, like masculine, weird, oversized, or even edgy/sexy elements to balance it out.

What worked

During the styling session, I tried everything from oversized outerwear to sheer skirts, trousers, and ‘belts’. Here are the winning formulas that transformed the dress from a closet mistake into a staple:

• The Oversized Layering formula: To combat the fitted, sweet waistline, throw something oversized and boxy on top. Layering an unstructured white jacket or a dramatic trench over the mini dress instantly modernizes it. You still get the benefit of a short dress, but the volume completely unsweetens the look. Add a pair of contrasting boots or loafers to ground it.

• The “Tucked-In” Trouser Trick (my fav!!): Inspired by my recent Balenciaga challenge, I tried tucking the tight dress straight into wide-leg trousers (like my Stellas). By pulling out a bit of extra fabric to create a long torso look, the dress transforms into a sleek, incredibly cool top. It’s surprisingly comfortable, practical for work, and completely reinvents the silhouette.

• Sheer Bottom Layering: Since I bought the dress in black partly to layer under sheer skirts, pairing it with a balloon sheer skirt or a contrasting white pencil sheer skirt added instant architectural interest. It turns a risky item into a wearable, textured outfit that feels intentional.

Final Thoughts

At the end of the day, playing in your closet should be fun. You don’t need to take every experiment too seriously. Some things (like my brief experiment with lavender cowboy boots or the peplum belt ring-dress) won’t work, and that is entirely okay!

The magic happens when you stop looking at an item as a static finished product and start treating it as a design element.

Are you holding onto any hard-to-style pieces in your closet right now? Let me know in the comments below what kind of items you want me to tackle next time!

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When we buy something new, our instinct is to ask: “How do I make this look good?” But trying to build the single, perfect outfit right out of the gate actually boxes us in. In this LIVE, we break down why styling is inherently a divergent thinking problem—meaning there is more than one right answer—and how you can train your brain to unlock hundreds of outfit combinations with one simple exercise.

Whether you’ve been eyeing a pair of sporty nylon pants, a fluid pleated skirt, or just want to get more mileage out of what you already own, this mindset shift changes everything.

The two ways to look at your closet

There are two distinct phases of building a relationship with your wardrobe:

• Phase 1: Starting from the Item (The Practice): You take a specific piece and figure out how to integrate it into your life. This is where everyone starts.

• Phase 2: Starting from the Vibe (The Advanced Level): You understand your clothes so deeply that when you get dressed and think, “I feel too masculine today, how do I undo that?” you instantly know exactly which piece will inject the perfect dose of femininity.

To get to Phase 2, you have to practice Phase 1. And that’s where the Rule of 7 comes in.

The challenge: The 7-Scenario styling exercise

In design school, we were forced to come up with 100 different uses for a single object to stretch our creativity. For your closet, you don’t need 100, but you do need seven.

Why seven? Because stopping at two or three ideas doesn’t force your mind to expand. Seven forces you to problem-solve.

The trick is to anchor the item to real-life functional goals in your routine. When you give your brain a specific destination, it unlocks creativity you wouldn’t find automatically. In the video, I put a pair of oversized, sporty Tibi pants to the test across my own life scenarios:

Why function drives Creativity

Notice how the outfit for the movie theater or the airplane came together? I would never have automatically paired that flannel shirt with those nylon pants if I hadn’t been thinking about the freezing temperature of a movie theater. Function drives the aesthetic.

You don’t need drastically different items for every look; sometimes, a simple snap of a button, a half-tuck, or a shoe swap completely transforms the vibe.

Over to YOU!

Carve out an afternoon, pick that one tricky item in your wardrobe, and write down your 7 real-life scenarios (school drop-off, coffee dates, work meetings, Sunday brunch). Don’t judge whether the outfits are perfect. Just explore.

Check out the full video above to see how these transitions look in real-time, including a breakdown of sizing up for a balloon-pant effect and how to play with visual conflicts in summer styling!

What’s the one item in your closet you’re going to try the 7-Scenario exercise with this week? Let me know in the comments! Also, should I make this a series? If so, what should I style next?

Okay, that’s a wrap for this one!

If something in here made you nod, send it to the friend who would also nod. That’s genuinely all I want, along with a few more things of course:

🔁 Restack or quote the part that hit, it helps more than you’d think. Especially since I don’t do paid subscriptions, Substack won’t push this one out without your help

💖 Like or comment if you have feelings (I will read every single one!)

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My friend, , recently posted about the marshmallow test. You know the gist: you give four-year-olds one marshmallow and tell them they can either eat it now, or if they wait a certain amount of time, they get two. Back when the study was first published, the hypothesis was that the kids who waited—showing an innate ability to engage in delayed gratification—had better life outcomes.

This has since been debunked. Modern research shows that a child’s ability to wait for a treat isn’t a silver bullet for future success. Instead, waiting largely reflects their socioeconomic background and environment, which also contributes to their success later on in life.

My friend equated this to shopping. Do you buy one dress now? Or do you wait and get two dresses later at the same price when it’s sale time? Which btw, just purely mathematically this has merit and also she posts great steals if getting more for less is your vibe (whose vibe is it not!!), do follow her. But I digress.

It got me thinking about what I would do, and honestly, my response was: both options suck. I want two marshmallows now. Everyone can be convinced. I would simply figure out how to make the scientists hand over the two marshmallows right away.

Now, on to my other random, seemingly unrelated story. But my dear reader, trust me, it comes together BEAUTIFULLY (if I may say so) at the end.

So: Chanel, Matthieu Blazy, Métiers d’Art. Wowowowow. I am not traditionally a Chanel person, BUT I am a bold-graphics-and-prints-presented-in-a-sophisticated-way person. The colors, the friction, the contrast—oof! I instantly fell in love with a specific bag and multiple pairs of shoes the moment the collection was presented.

However, there was a problem. I might be new to Chanel, but I am a veteran in these retail games. I personally have never had to play the Hermès “game” (where you buy thousands of dollars of stuff you don’t actually want just to get the thing you do), but I’ve still managed to be successful in getting what I want just via relationship building (genuine relationship, not code for spend $).

But how do you build a relationship between now and the time a highly anticipated collection drops in stores? They are going to make tiny quantities; boutiques will get minimal allocations. What could I possibly do or say to make them sell what I wanted to me, vs. the VVIP clients they’ve had relationships with for years?

I did not know. But I knew I would figure it out.

The Audacity framework

Ladies and children of ladies, this is where the sheer audacity comes in. Audacity is one of the key ingredients to success, IMO. And audacity is not something traditionally bestowed upon little girls (and women, eventually).

One of my favorite books is Brave, Not Perfect by Reshma Saujani. In it, she argues that little boys are taught to be brave, while little girls are taught to be perfect—often coming from a place of love and protection from parents. It’s a father’s natural instinct to protect his little girl, but what that translates to in adulthood is less risk-taking and more measured, cautious actions in women.

OK, now I will lay forth another belief: How you do something is how you do everything.

The world needs rule followers and rule benders for that perfect balance. And I personally believe we need more women to be rule benders.

Is it a must that you shop luxury to become a rule bender? Duh, of course not. Fuck that, it’s obviously not the most important problem in the world. BUT, if you are someone who desires that bag, those shoes, or that gorgeous jacket, and the only thing holding you back is limiting self-beliefs, high-end retail is a GREAT, low-risk area in your life to practice these skills.

Here are the exact mindset shifts you need to navigate these luxury houses, and the traps people fall into instead:

• Shift 1: De-escalate the paranoia. I will not hold negative beliefs about the people working there. They are NOT snooty. They do not hate me or people like me (brown people). They are not trying to gatekeep, and they are not out to get me. They are simply doing their jobs. When you assume people are out to get you, you show up defensive, closed off, and prickly.

• Shift 2: Drop the entitlement. You are NOT entitled to that bag. You are not entitled to that promotion, either. While it might feel “fair” that anyone walking into a store with money should be able to buy whatever they want, I do not judge these corporate systems morally. Bitching about how unfair a system is gets you absolutely zero marshmallows. It is about understanding the system as it exists, learning its rules inside and out, until you are in a position to bend them.

• Shift 3: Quit posing. Energy is so incredibly visible. I fully believe it is a noticeable, awkward tradeoff the moment someone starts pretending. Name-dropping, casually bringing up your vacation to Monaco, trying to prove how much money you have—it is simply not necessary, and it reeks of insecurity. True confidence doesn’t need to flash its resume at a stranger.

• Shift 4: Opt out of stack-ranking. Anything is possible. No one is better than me, and no one is worse than me. This last part is incredibly important. If you believe there is a stack-ranking of human beings—meaning you think you are above some because you are wealthier, skinnier, taller, whatever—you will also subconsciously believe you are below other people. Opt out of this system of comparison altogether.

• Shift 5: Own your frequency & worth. I am worthy of anything I set my mind to. If something doesn’t match my frequency, I wouldn’t desire it anyway. Nothing is holding me back.

• Shift 6: Reframe rejection. A rejection does not reflect on my worth. Systems exist; they operate how they do. A rejection simply means I haven’t worked out the logistics of the system yet. It is an invitation to try another way in.

• Shift 7: Be willing to be seen trying. Part of the ‘perfect girl’ curse is wanting everything to look effortless. We don’t ask for the rare item or the big promotion because we are terrified of looking desperate, or worse, being told no in public. But rule benders don’t care about looking cool; they care about the outcome. I had to drop my pride and be willing to look like someone who wanted those damn marshmallows.

Now, I want you to temporarily forget we are talking about luxury shopping. Think about any desire or ambition you have in life right now—whether it is a promotion, a new job, or just a better relationship with your kids. Read those self-beliefs and traps again.

Funny how it all applies, huh?

When I talk to women about this (luxury shopping), the number one concern I get sounds something like this: “I went into a boutique once when I was tired, messy, and running errands. The energy felt entirely dismissive until I pulled out my credit card. I shouldn’t have to ‘prep’ or dress up just to show a stranger that I’m important enough to be served.”

I deeply validate that feeling, we have all felt that cold, intimidating prickle in certain environments. But look at the mechanics of what is happening under the hood when we think that way. The moment you decide an environment is exclusive or snobbish, you have subconsciously positioned yourself as an outsider. You enter the room defensively, wearing invisible armor, almost waiting for them to prove you don’t belong because that would mean you were CORRECT. You assume they are stack-ranking you based on your outfit or your background, so you stay quiet, wait for them to validate you first, and interpret their standard, busy retail pacing as a personal insult.

This is exactly why you will never find a style guide or a what to wear checklist in any of my advice. I don’t care if you’re in a tailored suit or sweatpants and a messy bun. Wear whatever makes you feel the most you. The real rule-bender move doesn’t require aesthetic prep. It requires internal prep. It requires you to drop the ego, stop waiting for permission to exist in the space, and show up entirely whole. You set the frequency of the room, you don’t wait for them to give it to you. And if you don’t believe that is possible, keep re-reading this till you do.

And look, this isn’t me telling you that you need to go buy a luxury bag. If consumerism isn’t your frequency, skip the boutique entirely. The bag is completely beside the point. But what I am about to show you in the rest of this story is a live case study. It is a real-time tracking experiment of how these energetic shifts play out when they hit a rigid corporate system. So even if you couldn’t care less about leather goods, watch the mechanics of the game of life. Watch how the rules bend when audacity enters the room.

So let’s get back into it. That said, if you’re going to read this entire thing and bitch about your moral superiority for not having to “jump through hoops for a bag,” please miss me with that comment. This is not written for you, you are better than all of us please sit this one out.

OK, Storytime:

I saw the collection, fell in love, and wanted the bag. Realized it would be hard to get. I have a busy life, so I put it on the back burner—a problem for another day.

As we got closer to launch day (if you’re on style social media, you know the vibe), I decided to wander into the Chanel boutique two days before the official drop. No appointment. Luckily, I went at a relatively quiet time and connected with a Sales Assistant (SA) whom I loved instantly.

Honestly, I love most SAs instantly, much like I love most people instantly. There is a catchy ‘cool girl’ meme circulating online right now about how you don’t owe anyone a performance of niceness. And I agree with that, especially if it’s fake niceness. But I truly think a major life hack is genuinely seeing the good in people by default, unless they prove otherwise, and approaching everyone with warmth. That’s the world I want to live in, so that’s the world I create. Energetically, if you believe whoever you are talking to is a genuine, good person, you will show up entirely differently than if you assume they are a snooty gatekeeper waiting to look down on you.

I also believe in extreme ownership. If an interpersonal interaction goes wrong, I assume I am 100% to blame. Not in a self-deprecating way, but an empowering one. Who is the only person I can control? Myself. What do I gain by assuming it was the other person’s fault and that they should have acted differently? Nothing. It’s a strategic move, not a self-flagellating one.

I bring this up because so much can go sideways on your first move with a new luxury house. A complaint I hear often is, “No one even said hi to me.” I have never had this happen. Why? Because I am never standing around waiting for them to say hi to me first. The moment I enter a store, the first thing I do is warmly greet the first person I see. They have NO OPTION but to talk to me. And if they still don’t, you know what my takeaway is? Not that they were rude and dismissed me. It is “oh they were just having a bad day.” I am not giving them grace in doing this, I am giving myself grace. I am not dismissible (and neither are you), so if this happens, surely it must be external factors. :)

Back to this day though, they did greet me back with a smile. So, I chatted with the SA. I was completely transparent with her. I told her I had no prior relationship with the brand, but I would love to build one because Matthieu Blazy is taking things in such a fascinating new direction. I explained the why behind my interest, and told her I was looking for Bag X.

She looked it up and told me they were only getting two, and both were already spoken for. Was this the absolute truth, or was she making it up because she didn’t want to hand a coveted piece to a walk-in? Irrelevant. I operate in response to the information in front of me, not my insecurities.

I asked her what loopholes might allow me to pull off a coup. She smiled and told me to come back at 5:00 PM on launch day. If one of the two clients looked at the bag and changed their mind, she could pass it to me. Awesome! Since launch day was a Tuesday, it made for the perfect after-work activity.

I went back on Tuesday. The moment she saw me, I could tell by her face it wasn’t good news. Both bags were gone.

I thanked her and asked if there was a waitlist I could join. She mentioned they were getting one bag designated for the window display, but it would be a while before they were allowed to sell it, and she didn’t know if they would ever get more stock although it was very likely. She offered to put me on the waitlist for that display model, but noted I was already third in line.

I thanked her again, and instead of leaving, I just stayed and chatted with her about the collection, the craftsmanship, and her personal favorite pieces. I think a lot of people wouldn’t do that because we place these environments on a pedestal and don’t want to “waste their time.” But is talking to another human being really a waste of time?

This needs to be done with a genuine love for human connection, not a transactional “if I talk to her, she will find me a bag” motive. She had already made it super clear there was no bag. At that point, I was just genuinely interested in her perspective on where the brand was heading.

Fifteen minutes later, as I started bidding her farewell, she paused. “Let me check something for you.”

She went to the back and came out to tell me there were exactly two bags left in the entire country that were not spoken for, and told me which boutiques had them. Aha! We were out of the dead end.

Both stores were on the East Coast. By this time, it was 9:00 PM Eastern, so I retired for the day to pursue the case the next day.

The next morning, I called Store A. The connection was terrible and I couldn’t hear the person, so I hung up and called Store B in NYC. They confirmed they had one unspoken-for bag. BUT, they couldn’t sell it to me over the phone—standard corporate policy. However, they mentioned that if I had a friend in the city who could come try to get it for me, that could work.

I hung up, and my mind immediately went to my friend, Dena.

Why her? First, you need a close enough friend who won’t mind doing you a massive solid on a weekday. Second, you need someone who is a persistent mfer. If there is anyone I trust more than myself to execute this mission, it is her. Her superpowers are simple: she doesn’t give up, she has an incredible ability to build genuine human connections, and she has a deep love for the hunt.

If I am a level 5 in audacity, this woman is a level 10. I DM’d her and asked if she was down. She said YES!

The Heist

My confidence was growing. Dena marched off to the store right away, clearing time for this in her incredibly busy life (shoutout to her for being a real one).

Because I was on my lunch break, I dialed into a live phone call to listen in like a remote getaway driver while Dena went on this mission. When Dena arrived and asked, the NYC SA obviously said the bag wasn’t available. Expected. They aren’t exactly incentivized to hand a high-allocation piece to a total stranger, and Dena wasn’t a Chanel customer either.

And then Dena did what I can only aspire to do. Truly, I feel blessed that I was able to eavesdrop on this masterclass. She simply created a connection with the SA right then and there. Total, genuine interest.

Again, this was entirely non-transactional. Dena wasn’t doing this to get a bag; we were past that now. She dropped all ego, pretension, status, and name-dropping. It was just human-to-human connection. Y’all, it really is that simple. I am convincing Dena to do a training on how to genuinely network without that icky transactional feeling we all hate, but in the meantime, notice how the magic happens when you simply show up fully present.

Forty-five minutes later, the SA told Dena they would text her later. My ears perk up on the line. Wdym text?

We found out that evening. Dena received a text from the SA telling her to come back the next day at 3:00 PM. Perfect—right around my lunch break again, so I could dial back in for Phase 2.

The rest of it played out like a total fairy tale. Dena went in, they brought out the bag, I talked to them over the phone to finalize the details, and they processed the shipment. As I sit here writing this, I am staring at the package on my floor, waiting to be unboxed.

And just to prove the theory of momentum: the very next weekend (yesterday), I was having brunch near my local Chanel store with a friend. As I was leaving, I texted my original SA from the beginning of the story to see if she was available at 2:00 PM. She was. I walked in, told her the saga of the NYC bag (she was absolutely shocked it worked), and then asked about the shoes I had also been eyeing.

Thirty minutes later, I walked out of the store with the shoes.

Which btw, I am styling these shoes all week on my IG:

Also, since you have read this far, do enjoy me dancing with the bag:

The Two-Marshmallow life

When I finally held that package, I realized something important. This wasn’t actually about the leather, the bold graphics, or the thrill of luxury consumerism.

This was about the scientists remember them? The ones in the white coats telling four-year-olds that they have to sit there and choose between one treat now or two treats later? The ones who built a system based on patient compliance, arbitrary waiting lists, and strict, artificial parameters?

Most of the world is sitting in that waiting room. We are waiting for the perfect time to ask for a promotion. We are waiting until we feel qualified enough to take a risk. We are waiting for the gatekeepers of our lives to notice how perfectly we are following the rules so they will finally hand us our reward.

But the gatekeepers are just people doing a job. The systems are just constructs. And the waiting list is usually an illusion.

On paper, I was completely unqualified for that allocation. I didn’t have the history, the profile, or the status. But I refused to stack-rank myself below the system. I dropped the pride, risked looking desperate, showed up with genuine warmth, and let audacity lead the way.

You don’t have to wait for them to grant you what you want, and you don’t have to wait for permission. You can walk right into the laboratory, look at the parameters of the test, and figure out a way to get exactly what you want.

Because how you do something is how you do everything.

So bag or not, this is just life. You press on, you fail, you get up and try again. Go bend some rules this week. Get your two marshmallows.

Okay, that’s a wrap for this one!

If something in here made you nod, send it to the friend who would also nod. That’s genuinely all I want, along with a few more things of course:

🔁 Restack or quote the part that hit, it helps more than you’d think. Especially since I don’t do paid subscriptions, Substack won’t push this one out without your help

💖 Like or comment if you have feelings (I will read every single one!)

🔔 Not subscribed yet? Subscribe, friend!

Find me on Instagram @astahearts for more outfit overthink-ery!