There’s a meme going around that says “sorry I can’t make it, all of my clothes look stupid on me,” and that stuck with me because as a men’s stylist, I know exactly which guys are relating to it right now. Fortunately for you, that ends today. We’re making you interesting, making you look good, and making sure girls actually notice.

There’s an entire category of guys walking around with a massive unfair advantage, and it’s not about money or genetics or height or great hair. It’s proximity. The musician, the actor, the creative director, they’re surrounded by other guys who are playing in the big leagues when it comes to style. And it’s not done in the flashy, buttoned up, or trying-too hard way. It’s so easy and effortless that it might not even make sense.

He’s the guy who rolls into his office at 11am in a chore coat and fatigues because nobody there is going to blink, then goes straight to a client dinner for steaks at American Beauty in Venice wearing jeans, a hoodie, and a trucker hat, and somehow looks like the only interesting person in the room.

He’s underdressed on purpose. He’s got tattoos, the rings, the tan that says he was somewhere outside recently, and even if he says maybe 4 sentences all night, every girl at the bar keeps looking over, trying to figure out what’s happening at his table and hoping to time their exit with his so they can cross paths on the sidewalk.

That guy isn’t better than you. He just has exposure to something you never got. He lives in Venice, or Brooklyn, or Austin, or a neighborhood where the guys at coffee shops barely work and somehow own a 3-story townhouse where he hosts a natural wine club every month on his rooftop. His friends are other creatives. They’re in bands. They work in entertainment. They work with high profile clients. He has a stylist, a hairdresser, a watch guy, a tailor he texts.

From his own social circle alone, his taste gets built for free just by existing there. He’s grabbing a bottle from Vin on Rose before a dinner party. He’s getting an iced cortado from Companion. He’s parking his Bronco outside Erewhon to grab some bottles of Loonen like it’s nothing, because to him, it is nothing. He’s not stuck behind a desk for 10 hours a day. He goes out and does things on purpose because that’s when he has his best ideas. He’s in motion.

Meanwhile, if you’re the guy in the button-up, the blazer, the chinos, the dress shoes, overdressing on dates and at the office, blending in with every other exhausted executive who’s coasting on a broken circadian rhythm, has never once hit his protein target, hasn’t worked out consistently since 2019, and is getting maybe 3 Hinge matches a month while wondering why. I need you to hear this. Being burnt out and boring is not a personality trait I will let you continue. That’s what happens when nobody around you is showing you a better way to live and that is 2020 behavior.

If you’re not surrounded by inspiration in real life, and let’s be honest, most guys in c-suite tracks aren’t, you have to go get it somewhere else. That’s what this is. Consider this your proximity into a cooler life because I know you need it right now.

You don’t need a closet overhaul. You need to stop dressing like a guy who’s been coasting and start dressing like a guy who’s actually paying attention, to his coloring, his proportions, the room he’s walking into, and, frankly, his life. Let’s fix that.

Behind the paywall, here’s what you’re getting:

• The cool guy’s early fall calendar with his rituals broken down week by week

• Insight into the Brooklyn, Malibu, and Texas Cool Guy, fully sourced, piece by piece, so you can copy the exact look no matter where you live

• The exact conversation openers that make you the guy people gather around, not just the guy who looks good standing there

• The proportion fix most guys have never once heard, the real reason your clothes have looked off this whole time

• What’s actually in for Fall ‘26 and a preview of the shift already coming in 2027

Why Your Clothes Look “Stupid” On You

If you ran into an old friend at a wedding and he asked what’s new with you, would you actually have an answer? Or would you need 5 minutes to remember the last time you talked so you could figure out what you’re technically supposed to catch him up on?

Meanwhile you’re mentally flipping through a completely blank calendar filled with late nights at the office, Uber Eats receipts, and 2 first dates that never became a second. Don’t even start with that work trip you took in March, thinking you can still stretch that out as your entire personality for the year. Most guys are bracing to bore everyone throwing small talk around with no substance for the next 10 minutes until the bar opens.

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I’m getting ready for a wedding tonight, and I have to tell you about last night first, because it reminded me of something you absolutely need to know.

Last night was the welcome party. This couple, and I mean this in the most sincere way possible, they’re insanely cute. Like, you can feel it when you’re around them. They have real chemistry and it’s not the performative kind at all. Same wavelength. Same page. He’s lowkey and chill about everything. He lets her shine, and somehow that makes him shine more, not less. They met on Hinge and now here they are.

So I’m talking to the other couples last night, doing my usual thing because I love hearing how people met, and I remembered something. I’ve heard this exact story so many times I could probably recite it in my sleep. Not just at events like this, but inside the entertainment industry when I was a television producer for over a decade. At important dinners, on sets, during casting interviews.

I used to work on this show entirely focused on CEOs. We got to know their whole lives including their wives, kids, intricate insight into their business minds and how they run their companies. While I was producing, I basically got adopted into their family for a few months at a time, saw their routines, hung out at their house and offices and got occasionally invited to their birthday parties. Like everything.

I always ask his wife how they met. She laughs, looks at him, and says, “I canceled on him 3 times.” It’s always three. Never 2, definitely never 4, and I genuinely didn’t know why the universe picked that number until now. They both laugh like it’s their favorite inside joke ever because by now it basically is.

Now when I look back on those moments, being someone who now works with men on their style and dating and image, there’s so much more happening underneath that laugh. It’s a very specific strategy and I’m going to hand it to you, because I don’t think you’ve ever heard it broken down quite like this.

Because here’s what I need you to actually understand before I even get into the mechanics of it. I have had so many of guys ask me things like, “what DM do I send, what’s the perfect opening line, how do I ask her out without sounding weird.” And every time, I think the same thing. You’re thinking too small right now.

Does a CEO sit around agonizing over the exact wording of an email before he sends it? No. He’s operating from the top. He already knows the value of his own position, and he knows exactly what kind of role is opening up in his life and what type of person deserves to fill it.

He’s not worried about making the first move sound perfect. He’s already thinking about something much bigger than a message. He’s thinking about the entire trajectory, the whole picture, what this person is actually going to mean for the next 20+ years, not whether the text has the right amount of casual confidence in it.

That’s the actual shift I need you to make before any of this will work for you. Stop treating the first move like it’s a wording problem. It was never a wording problem. It’s a positioning problem, and once you understand that, the DM stops mattering nearly as much as you think it does. Here’s how it’s done:

The Deal Nobody Taught You How to Make

She wasn’t sure about him at first. He wasn’t her type, not even close. She was in her single girl era, out with the girls every weekend, building her career, not exactly hunting for a husband, more just living her life and figuring out who she was while she did it.

Then he shows up, and he’s different from every guy she’s been half-dating. He’s serious. He’s put together. He’s running something, whether that’s a company or a career or just his own life, and he is decidedly not at the bar with his friends on a weeknight. He’s at dinners, events, meetings. He’s building something. And some part of her doesn’t know what to do with that yet, because it doesn’t match the guys she’s used to.

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Quick personal note before you hit play because I’ve genuinely been waiting to say this. Remember when I mentioned the podcast was coming? It’s here. You’re still getting everything from me you already get: the posts, the outfits, the playbook. None of that’s going anywhere.

But starting this week, you’re also getting my actual voice, in your headphones, in your car speakers, wherever you take me with you. Longer than 60 second reels and much deeper than style content.

Because truthfully, I’ve been sitting on this for a while, wanting to tell you what’s actually working on her. Other than natural wine, trucker hats, iced cortados, and the cool guy’s standing reservation at Gjusta, of course. Some things just hit different when you hear them, and I need this one to actually sink in.

So here’s what’s coming. This is what goes through her head when she meets you, the things she’d only ever admit to her group chat, the ones that never make it back to you. Because once you know how she thinks, you start becoming someone she has to figure out. And that’s exactly what gets her hooked.

It’s not a traditional podcast, exactly. More like intel girls never want you to have. And some stories about the guy in the vintage Bronco I’ve never quite gotten over, the ones I’ve been saving (because I’m hoping he doesn’t see this).

This has been a long time coming. I’m excited for you to finally hear it.

xo Lisa 🍒

P.S. Find me on Instagram here.

Somewhere out there is a guy in a vintage Bronco who’s never had to try. Every girl in the room knows it’s him before he says a word. She spends the rest of the night trying not to look over again. Nobody agrees on what it is exactly, just that they felt it and couldn’t explain it. RÒWE REPORT is a weekly dispatch from Lisa Rosen, letting you in on the secret.

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New series starting today. We’re going room by room, breaking down exactly how to build the cool guy’s apartment. You know the one. She walks in and something in her stomach drops a little because it doesn’t fully look like a guy lives here alone. It looks like he has a hot ex, the kind with actual taste, high standards, and opinions on Le Labo candles.

Suddenly, your new girl is a little worried that she might not be good enough for you. We’ll let her shake a little. That’s how it works when you have your apartment aesthetic dialed in. She assumes there have been other girls before her. Because once she sees Parachute sheets, coffee table books, and natural wine in your fridge, it’s game over.

Don’t be shocked if you start getting double texts after this. Let’s start with the living room.

I’ve been styling men’s homes for a few years now. There’s one thing I see almost every single time I’m in a guy’s place. A guy moves in, and within the first 2 weeks, he usually orders everything at once, getting almost everything fro the same 2 places.

The couch, rug, coffee table, all in the same 3 shades of gray or navy. Instead of focusing on how the room is going to feel, he’s usually fixated on where to hang the TV without seeing any issues that it’s taking up the entire wall.

He hits checkout on 4 different tabs and by the weekend the whole apartment looks like it’s one flat color. That’s not a bad thing, like it’s live-able, but it’s missing the most important part: the vibe. And then he doesn’t think about it again for 6 years.

But what actually happens in those 6 years? You get older. Your job changes. Your friend group changes. You start caring about things you didn’t used to care about. And then one day you meet a girl who is not messing around, she’s girlfriend material, maybe wifey, and she wants an actual adult relationship.

But you bring her home and you suddenly see your own apartment through her eyes for the first time since you moved in. The Bed Bath and Beyond comforter you bought on sale that came in a plastic case with a zipper.

The couch you got off Facebook Marketplace in 2019 that you’ve never once cleaned. Or the art you never actually hung up because you never actually got it framed. And you think, ‘Oh shit.’

Is she going to find out that you don’t have your life together????

Your apartment is the first dead giveaway. (I’m not saying you don’t have it together, but if you don’t have a real aesthetic happening, it just doesn’t look great for you).

Girls judge you based on your apartment. I’m being honest and you wanted the truth. It doesn’t matter if you make $300k/year and you drive a BMW. If your apartment has a weird, post college-adjacent vibe to it, something is going to feel off.

And she’s going to describe it to her friends and her mom and her co-workers, and they’ll hear the confusion in her voice because she really liked you. But maybe your maturity level is about 10 years behind where she thought it was. Don’t hate me for saying this! This is just how girls think!!

Your place tells her exactly where you are in life, whether you meant it to or not. She’s not sitting on your couch thinking “okay, I’m sinking into this cushion, but he has potential.” She’s picturing herself there on a random Tuesday 6 months from now. She’s picturing hosting Friendsgiving in your kitchen with her friends.

She’s wondering if there’s an actual table with actual chairs where you’d eat dinner together, or if you eat standing up at the counter like it’s a frat house.

Your apartment is either telling her you are ready to build a life with someone or it’s telling her “I have not upgraded a single thing since college.” She can tell the difference in about 4 seconds. Like, please tell me you do not use paper plates.

So let’s start with the living room because it’s the first room she sees and it does the most work for you.

Room Tour: Beachwood Canyon

I styled a living room a couple months ago in Beachwood Canyon, and it lives rent free in my head now. We went with an olive green sofa, low and deep, the kind you fall into and immediately regret every plan you had for the rest of the night.

There’s a giant art book cracked open on the coffee table like he was just casually flipping through it, not like he ordered it 2 days ago and staged it 45 seconds before she rang the doorbell.

An oval rug underneath the whole thing, which sounds like a small detail except most guys have a rug that’s way too small and barely fits under their couch or no rug at all. We layered it over a bigger jute rug.

There’s vintage pottery on the console that looks like it survived several eras and multiple situationships. A vase that isn’t trying too hard. Zero overhead lighting on, obviously, because we don’t do interrogation-room lighting in your apartment. There’s a dog bed in the corner and it actually adds to the room’s character.

Walking into this room, it smells like leather, cedar and slightly overpriced ceramics, which is a scent now and it’s working. Nothing matches on purpose and the room as a whole feels unique, not mass produced, which is the whole point.

This room isn’t saying “I just moved in and panic ordered a starter pack.” It’s saying “I have taste, I have a life, and yes, I actually open my coffee table books.” Don’t worry if the last part is a lie. No one will know.

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How To Build The Ex She's Worried About

Real talk for paid subscribers only. I’m giving you my insider tips on what you actually need and how to build the vibe, so girls instantly view you as “boyfriend material.”

This is the actual cool guy’s apartment playbook. The one I use when a client calls me after closing on a place in Venice or the Palisades and wants it to look like he’s lived a whole life there already, not like he just wired a down payment 3 weeks ago. Nobody’s mattress is on the floor as their starting point. This isn’t a taste problem or a budget problem. It’s a time problem.

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I went out for the first time in awhile this past weekend for my friend’s birthday, and I have to talk about what he wore because it’s stuck with me all week. Black tank tucked into black trousers, a…

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Hey. I know. You haven’t heard from me. I didn’t mean to become the girl who goes hot and cold, ugh. Like we had a really good date and then you didn’t hear from me for a few weeks. I know, I know. It’s so unlike me. But I’m back now. Are we still good?

The end of summer in LA is the absolute best part of the year. I’ve been going to the beach with Murph in the mornings, waking up early, and starting a little podcast for you (don’t jinx me, I get really in my head about how my voice sounds lol, but it’s coming soon).

In the meantime, let’s get you caught up on the cool guy and his style for early fall. He’s got four things on the calendar that I happen to have some insight into, and I’m not going to explain how. Let’s just say I have a source.

The thing about the cool guy is he never narrates his life before it happens. He doesn’t post a countdown story or build anticipation for anyone. He just shows up somewhere, already dressed exactly right, and lets everyone else find out later.

Four events. Four different rooms. Same guy looking better than everyone else. Here are his outfits and that’s all I’ll say for now.

Outfit links are below.

LOOK #1: THE DINNER PARTY

Someone’s hosting in Los Feliz, the kind of night where everyone brings a bottle and nobody leaves before midnight. He forgot to RSVP and was the last one there. But they saved him a seat anyway.

The Look: He’ll wear a brown camp shirt left open over a white tank, faded denim, and boots that have been to better places than this backyard. He’ll bring a bottle nobody’s heard of and somehow it’s the one that gets finished first. By the time dessert comes out he’s already helping clear plates, and nobody remembers asking him to.

GET THE LOOK

LOOK #2: THE BACKYARD HANG

There’s no real plan, just a group chat that said “come through” around 4pm. He’ll show up 2 hours later with nothing but himself and somehow still be the reason people stay till dark.

The Look: He’ll wear a cardigan over a white tee, cream painter pants with a story nobody asks about, and black boots. He’ll sit on the arm of whatever chair is closest, never actually taking a seat, like he’s ready to leave any second even though he stays the longest.

GET THE LOOK

LOOK #3: DATE NIGHT

He picked the restaurant, no group text, no asking around. He already knew where he was taking her before she said yes. Drinks at Gran Blanco. Dinner at Market in Venice. Yes, he’s wearing shorts. It’s Venice.

The Look: He’ll wear a camp shirt, a gold necklace that never comes off, tailored shorts, and boots that make a statement even in September. He’ll get there early, already have a table, and stand when she walks in. Small thing. Nobody does it anymore. He still does.

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LOOK #4: THE CONCERT

Some band he’s been talking about for months that nobody else has heard of yet. He’s taking his new girl and she picked out her outfit 5 days ago, but would never confirm that.

The Look: He’ll wear a chore jacket over a graphic tee, camo cargos, and a trucker cap he’ll take off exactly once, for the encore. He’ll end up near the back by choice, not because he couldn’t get closer. He just likes watching everyone else lose it first.

GET THE LOOK

Anyways, that’s all 4 for now. Four rooms, one cool guy, and the same instinct for showing up exactly right without ever announcing it. More fall outfits are in the works. If you have any events coming up or have requests for upcoming posts, just reply.

Until next time boys,

xo Lisa 🍒

P.S. Something to play while you drive up the coast pretending you have somewhere to be, here is my Pacific Coast Highway playlist. Enjoy the ride.

RÒWE REPORT is where I write about modern love, men’s style and everyday life; the objects, choices, and relationships that shape who we become without announcing themselves. This is for guys who appreciate the details and trust their instincts. If you’re here, welcome. You’re exactly where you should be.

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Okay, I do have some very light expectations for you. I simply expect that you read each Substack I post from beginning to end, which means you already knew the Summer Dating Edit was coming, right? If you didn’t, that’s your sign to get caught up here. Am I asking for too much!?

Now let’s get down to business. So I have a friend. One of my hottest girlfriends, and she went on a date with this great guy recently. He’s an art dealer, very put together, amazing style. He was checking every box.

They met at this cool restaurant in Venice on a Friday night. She loves this place. She had her outfit all picked out, scheduled her Uber, and updated the group chat on the whole play-by-play. Everyone was highly invested.

So she gets to the date and from the second they sat down, he revealed somewhat of a plot twist: he had other plans. It went something like, “I have to get out of here around 8PM, my buddy planned a dinner party later.”

Uhhhhhhh. As you can imagine, this came as a shock. Now, they had matched on Hinge, they messaged for a few days, they added each other on Instagram. Enough banter and rapport was established for her to assume this date was the dinner.

And if we backtrack, that’s where it was a little vague. When he set up the date, he never said “dinner,” but given that it was a Friday night, she assumed.

“Let’s meet at Market around 6:30” were his exact words, I believe.

As someone who works exclusively with men on their dating lives, this date setup moves us into some gray area. I like when men are very direct with making the plan. They make the reservation, set the location, choose the time, send a confirmation text, etc. There’s a whole protocol.

But this one was purposefully vague, which I don’t love. “Let’s meet for dinner?” Love that. “Let’s get drinks at 7PM.” Sure. “I want to see you. How’s dinner / drinks at Market?” Brilliant.

But this guy chose a restaurant (not a bar), booked a prime dinner hour, and booked her on a Friday, one of the most desirable nights of the week.

So from the beginning, this made her feel like their date wasn’t his main event. In her eyes, he was using it like a pre-game for something else. And look, I would give this guy a little grace if he had mentioned it from the beginning, if he was setting the plan with a genuinely busy schedule and really wanted to see her anyway.

There are a few variations where the double-booked night could slide, but this particular case didn’t qualify.

So from that point forward, she felt incredibly awkward on the date. They ordered drinks and some light bites and of course the service took forever. Of course the restaurant was extremely busy. Of course it was loud and they could hardly hear each other.

And to make matters worse, he was stressing about the time the entire date. Sometimes a 1.5 hour date feels like enough time, but other times, when you’re at one of the most popular restaurants on a prime night, it takes 15 minutes just to get seated.

So the night ended up being a disaster. They never really hit a good stride in their conversation, and not only did she not want to go out with him again, she was ready to swear off dating at that point.

This is what happens for girls, and it’s highly important you pay attention. By the time you’re going on a first date with your dream girl, she has been on so many let-down dates like this one that, by the time you show up, you’re not just being compared to some idealized version of a boyfriend.

You’re being compared to the art dealer. To the guy before him who cancelled twice and rescheduled a third time like it was nothing. To the one who couldn’t recover when the conversation went quiet and just let it die there. She’s not grading you on a scale of 1 to 10.

She’s grading you on a curve against a rotating cast of guys who couldn’t get the basics right, and most of you have no idea how low that bar actually is. That’s not a compliment to them. That’s a very strategic opening for you.

So here’s what we’re doing with that opening. Inside the Cool Guy Dating Edit, I’m breaking down the exact 3 variables that separate the guy she deletes the number of from the guy she’s telling her friends about:

• What you wear and why the timing of it matters more than the outfit itself

• How to actually run a date so she’s not doing the work the art dealer left on the table

• The exact move for when your banter goes quiet and your brain forgets every word you know

This is some of the key parts I usually only walk my 1:1 clients through, the stuff that turns “great on paper” into someone she can’t stop thinking about. Consider this your fast-tracked version.

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The Cool Guy has a routine. He’ll never call it that. He just washes his face in the morning because that’s the first thing that happens, before coffee, before his phone, before anything else gets to…

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“He’s so cute, right? He actually opens the door for me every single time.”

Your new girl is in the kitchen at someone’s housewarming party, spritz in hand, telling her friends all about you. You’re…

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I probably shouldn’t say this much about the cool guy’s summer, but I do, and I’m going to tell you anyway. He’s got 4 weekends coming up that I happen to have some insight into, and I’m not going to…

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A lot of guys think that celebrities don’t have real problems when it comes to dating and relationships. Like the rules just don’t apply to them. And honestly, most of the time, that’s true but not i…

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There comes a time in your late 20s, mid-30s if you’re from LA, when the calendar starts filling up differently. Friends are getting married. Some of them are moving out of state. Others are buying h…

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Summer is the best time to be single. Everyone is outside, everyone is social, everyone is in a good mood for about four months straight and then it’s over. The weather changes, the energy shifts, and suddenly everyone who figured it out over the summer is coupled up just in time for the holidays.

You’ve seen it happen. New couples emerging in October like they planned it. Thanksgiving with someone who actually wants to be there. A New Year’s kiss that isn’t a logistical problem.

That window is right now. And if you’ve been sitting on your dating app situation, putting it off, telling yourself you’ll get to it, this is the one. Miss this window and you’re back to swiping in November when everyone is already emotionally spoken for and the selection has thinned out considerably.

Here’s the thing though. Most guys treat dating apps like a hobby with no end goal. They swipe when they’re bored. They match and let conversations die. They go on a date or two, nothing clicks immediately, and they go back to the queue. And then they do it again. And again.

And before they know it they’re 47 years old, still swiping their summer away like a plastic bag floating through an American Beauty scene that nobody asked for.

You need to think about your dating life the way you’d approach anything else that actually matters to you. With a strategy. With an end goal. The goal is a girlfriend by Thanksgiving. That’s the prize. That’s what you’re walking away from this game show with. Everything else, the matches, the dates, the conversations, they’re all steps toward that. Not entertainment. Not something to do when you’re procrastinating. A real thing you’re actively working toward.

But here’s the problem. Most guys have no idea how girls actually use dating apps. And I don’t mean that as an insult. I mean it literally. You’re operating based on your own experience of the app, which is completely different from hers, and because nobody has ever explained that to you, you’re making decisions that make total sense from your side of the screen and make zero sense from hers.

So before we talk about your photos, your prompts, your opening message, any of it, we need to back up. Because none of that works if you don’t understand the environment you’re actually operating in. And once you do, everything changes.

Here’s what’s actually happening on her end.

When a guy opens a dating app, he’s usually swiping. He’s hunting. He’s going through the general database, one profile at a time, making quick decisions. It’s active. It takes effort. Most guys spend a real amount of time on the apps because that’s how the apps are designed for them.

Girls use the apps completely differently. She’s not spending hours swiping through the general pool. The first thing she does when she opens Hinge is go straight to her likes. And if she’s attractive, she has a minimum of 150 of them waiting for her every single day. On a good day it’s significantly more.

She’s not getting through all of them. She’s going to scroll through, eliminate the obvious nos in about two seconds each, and maybe give genuine attention to 10 or 15 before she puts her phone down and goes back to her life. The rest of you are still sitting there in her queue, unseen, waiting.

This is the environment you’re operating in. And now that you know that, here’s how to use it to your advantage.

Get Into Her Likes First

Since you now know she’s going straight to her likes and not the general pool, your first job is to make sure you’re already there waiting for her. This is where proximity comes in and most guys completely ignore it.

Upgrade to premium immediately. I know, I know. Just do it. It will be the best $30/month or whatever you spend because it will actually save you hundreds on zero connection dates that could have been avoiding if you had better options. When you do upgrade, use the preferences and set your radius to the smallest possible option first.

Do not set your radius to 100 miles and consider driving to Las Vegas for a bottle service girl when you live in LA. The hottest people on dating apps almost always have their radius set to 5 miles. They’re not looking for a long distance situationship. They want someone who can actually show up on a Tuesday.

Hinge will still show you more people beyond that but starting small puts you in front of the people who are nearby, actually available, and actually the caliber of person you’re trying to meet. Quality over volume every single time.

When you like her first, you pull yourself out of the general pool and land directly in her likes queue. You’ve already removed yourself from the noise and placed yourself in a more curated subcategory. That’s the one she checks first. That’s exactly where you want to be.

This is where it actually gets interesting. Your prompts, your photos, how to message her when you match, what to say when her profile gives you nothing, how to read her energy, and exactly when and how to ask her out so you don’t lose the whole thing right at the finish line.

👇 Keep reading with a paid subscription where you’ll get the full dating playbook, weekly outfits, full style breakdowns, and everything else you need to become the guy she keeps telling her friends about. Be ready. 👇

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Let’s talk about your office wardrobe. And I say this with love. Most guys are not dressing like a guy who gets the promotion. They’re not dressing like a guy who gets the girl in marketing to look up from her laptop. They’re dressing like a guy who bought 5 things from a department store sale the week before his first day and has not revisited the situation since.

That was 6 years ago. Those fitted pants know it. The tight button down knows it. The suede Chelsea boots he thought were a thing in 2019, they especially know it.

Here’s what’s interesting though. The Cool Guy is not spending more money than you. He’s not working harder than you. He’s not even thinking about it that much. He just figured out the formula early and now it runs on autopilot. He walks into a meeting and something shifts in the room. His boss notices. The client notices. The girl in marketing definitely notices. And he didn’t do anything except get dressed correctly.

That’s what this is about. Getting dressed correctly, so you just know you look good and don’t have to overthink anything.

I’ve put together 5 outfits that will actually serve looks. For the office, for the coffee before the office, for the drinks after the office that turn into something you definitely can’t tell your co-workers about. And because there’s a small window right now between Memorial Day and summer where things are actually on sale (not that you care about that, not even a little), this is the time to dial in your signature look.

Don’t save this post and forget about it. That’s exactly what the guy in the suede Chelsea boots would do. Don’t be that guy.

Click each outfit for links.

MONDAY: THE MONDAY STANDARD

This is the outfit that walks into a Monday morning meeting and immediately gets taken seriously. Here’s how it works: the stripe shirt goes on first, collar slightly open, never buttoned to the top unless you want to look like you’re about to board a flight in 2008. The navy sweater layers over it for about half your workday. After lunch, the sweater comes off, sleeves get rolled up, forearms make an appearance. Girls always think this is hot. It’s not an accident.

The olive pants are doing more work than you realize. The break should hit just above the shoe with a slight ankle reveal, always with a crew sock. A bare ankle in the office is not a personality trait, it’s a mistake. And while we’re here: the backpack ends today. It’s giving first grader, lunch his mom packed, big dreams and a Pokemon keychain. The tote replaces it permanently. No further discussion.

TUESDAY: ON DUTY, ON POINT

There are industries where jeans are acceptable and industries where they are not. You know which one you’re in. But if you’re going to wear denim to the office, the rule is simple: the darker the better. Vintage black, washed black, the darkest blue imaginable. Light wash is for the weekend. Black denim is sophisticated. There is no in between.

This outfit proves you can wear jeans and still look like the most put together person in the building, but only if everything else is intentional. Black knit over a clean white tee. The tee should be fitted but not tight, the kind that looks expensive even if it wasn’t.

Now let’s talk about Common Projects. They had their moment in 2018 and some think it passed. I disagree, specifically in an office context. Because here’s what happens when a woman sees you wearing Common Projects: she ticks a box. Style. Taste. Invests in quality. Knows the difference between a good shoe and a generic shoe. There is a significant difference between the guy wearing Common Projects and the guy wearing Cole Haan. Please know the difference and please act accordingly.

The structured bag and the watch close the loop. Without them this is just a guy in jeans. With them it’s a statement. The hot girl in marketing can’t explain why she keeps looking up. It’s this. It’s all of this.

Before we get to Wednesday, a quick interruption. I have two fully updated Cool Guy Style Guides with 60+ outfits between them, my most detailed style notes, tons of visual inspiration and over 200+ links, all ready to shop.

The Essentials Guide has 9 office combinations inside and works for every age group including if you’re 40+ and wondering if you can still pull this off. You can, and you will.

The Summer Guide takes you into the weekends. If you’ve made it this far and you’re still wearing the button down from 2016, this is your sign. Both guides will save you hours of shopping and pay for themselves the first time she notices you.

Get the Style Guides

WEDNESDAY: THE BOSS

This is the outfit for the guy who walks into a room and people assume he runs something. The olive overshirt is the move, replacing the blazer for anyone working in creative, media, or tech, and honestly it’s better. I need to address something while I have your attention: the jeans, blazer, and sneakers combination needs to be retired immediately. That look peaked in 2018, it was questionable then, and I don’t want to see it at the office, at work drinks, or at a networking event. We’re done with it.

The overshirt is relaxed enough to feel lived-in and structured enough to feel intentional. Underneath, the same stripe shirt from Monday, because when something fits this well you own multiples and you don’t explain yourself. The charcoal trousers are non-negotiable. This is the look that belongs in a client meeting or a corner office. The pant sits at the natural waist and breaks clean at the top of the shoe. Get them tailored. I promise you it will change your life and it costs less than dinner.

The Shinola watch is the detail that makes someone look at you twice. It doesn’t say I’m trying. It says I’ve always been like this. One spray of Jack Henry Balance on your wrists on the way out. You’ll leave the office smelling like someone she’s going to think about on her commute home.

The last two outfits are the ones she’s going to bring up at brunch.

👇 Keep reading with a paid subscription where you’ll get weekly outfits, full style breakdowns & dating advice she actually wants you to have. You’ll become the guy she keeps telling her friends about, so be ready. 👇

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My brand new Cool Guy Summer Style Guide just dropped and before it officially gets announced, I wanted you to have it first.

This one is different from the Essentials Style Guide. It’s not about building a system or learning style rules. It’s about dressing for the life you’re actually living this summer. The coast. The road trip. The outdoor dinner where the light is golden and you want to feel exactly right for the night. The city in August when everyone else left. The slow Sunday that turns into the best day of the week.

I built this guide for the guy who’s about to have the best summer of his life and wants to look like it. The looks are relaxed and unexpected. The combinations are the kind that make people notice without knowing why. The loafer with the shorts. The trucker hat that makes her friends refer to you as “hot hat guy”. The one outfit that makes every other guy at the table quietly aware they need to do better.

Inside you’re getting a 70+ page PDF download with 30+ complete outfit breakdowns. 170+ linked pieces across 30 categories with tons of visual inspiration. It works whether you’re in California, New York, Texas, Italy, London, or anywhere in between. Everything is linked and shoppable directly from the guide. Each piece was hand selected by me personally.

Here’s your first look:

Clothing Directory:

30 categories covering everything you actually need this summer. T-shirts, graphic tees, tanks, resort shirts, overshirts, jackets, trousers, jeans, shorts, denim shorts, swim, loafers, boots, sneakers, sandals, hats, sunglasses, jewelry, fragrance, and more. Every single piece is linked so you can shop straight from the guide. No searching, no tabs, no second guessing.

30 Styled Outfits:

10 complete looks built around the moments that define your summer and 20 more outfits assembled by environments. Each one has a personality. Somewhere Coastal. Gallery Guy. Golden Hour. No Return Flight. Nights Out. Every look comes with a description that tells you exactly why it works and what she’s going to notice first.

Outfit Assembly:

This is where it all comes together. Five environments, coastal, city, date night, travel, and weekend, each with multiple complete looks showing you how the same pieces work differently depending on where you’re going. Pull it up when you’re getting dressed. It’s that easy.

It’s $75. But my paid subscribers are getting it 30% off through July.

The code is below. Paid subscribers get early access as a thank you for being so hot and cool. 👇

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I was 26 when I first understood that LA had a version of itself I hadn’t seen yet.

We had just won an Emmy for the first season of a show I was producing. I remember the specific weight of that momen…

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When I was in high school, there was this guy everyone had a crush on. Football team. Nicest guy. Life of the party, drove a truck, and was so genuinely modest about all of it. Never the ego type. He was the friends with everyone type who never really talked about himself.

So when he threw parties or had people over for his pool on hot valley nights, everyone was kind of shocked to discover he had a full recording studio built into his house. Side hobby: music producer. He played every instrument. Self-taught. Completely casual about the whole thing.

When I wrote about tall athletes lacking depth last week (full post is here), I meant it but there are always exceptions. Part athlete, part musician was a winning combination. And now, years later, I thought of him. Because he wore the best cologne I have ever smelled in my life, and I finally found something close to it.

He never told me what it was. I asked him so many times. He’d say, “I made it myself. I blend a bunch of scents,” and leave it at that. He promised one day he’d tell me. I’ve been trying to figure it out ever since.

If you want to go even deeper on this, I wrote a Cool Guy Signature Scent Guide with a more technical breakdown here:

So now that I style men, I’ve built a formula for you. One that women love, men want, and somehow draws everyone in by doing almost nothing. There’s real history behind it. It’s a 3-layer system: Base. Anchor. Seal.

Just add salt, sand, and a tan and this will carry you all the way into summer. Learn this once and it will completely change the way she remembers you.

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Step 01 : The Base

This is your foundation. A body lotion or body cream. Something that locks in moisture, makes your skin look sleek, and sets the stage for everything coming after it. Most guys hesitate with lotion because they hate how it feels. The trick: apply it straight out of the shower while your skin is still slightly damp. There’s no stickiness. And these are high-quality formulas, not drugstore consistency.

Try This:

• Bergamot & Hinoki Body Lotion — Salt & Stone

• Saffron & Cedar Body Cream — Salt & Stone

• Resurfacing Targeted Body Lotion — Grown Alchemist

• Hinoki Body Cream — Le Labo

• Hinoki Hand Lotion — Le Labo

Body cream is slightly thicker than lotion and more moisturizing. Both work. This one comes down to personal preference.

👇 The full post is this way. 👇

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He pulls on a pair of olive shorts, a vintage tee that’s been washed enough times to feel like a second skin, slips into his Gazelles, grabs his sunglasses off the counter. There’s a bottle of natural wine already chilling. He’s texting the girl he met at Gjusta on Saturday, “Pick you up in 10.”

They’re heading to the beach. There’s not a full plan, just enough of direction for her to wear shorts, sandals and a hoodie if the breeze picks up. That’s the whole point of spring. The days are long enough now that you can just go. The cool guy rarely turns down an opportunity to watch the sunset from the beach.

This spring edit is built around that version of you. Everything worth wearing right now across the most important categories. Go through it slowly and notice what you keep stopping on. The colors that feels right. The shoes that fits the lifestyle you actually want to be living. Then go look at what you actually have and be honest about it. Spring has a way of making the gaps obvious. It’s a good time to close them.

Spring Rituals

Before we lay out your pieces, let’s dial in your rituals. If there’s one promise you’ve made to yourself, it’s that you’re not skipping the farmer’s market this spring. Every Saturday morning, you’re there, wearing faded Levi’s, a trucker hat, and a loose t-shirt. The hot girl who makes sourdough out of her Topanga cabin has your loaf reserved.

Your beach day starts at 4pm and ends whenever. A long lunch somewhere with a patio that gets good light. A road trip up the coast that was decided on a Wednesday and happened by Friday. The Dodgers game where the tickets came through a friend of a friend. A Sunday that involves a dog, a hike, and nothing scheduled after 2pm.

The girl you’re seeing thinks you’re spontaneous. You kinda are and you’re kinda not. You just prepared quietly. The reservation was already made. The outfit was already right. That’s how you’re going into this season. No calendar invites, just a loose plan with follow through. The cool guy is at his best in April and May, right in that window before summer turns it into a whole other thing.

Now let’s build your spring style rotation.

The Hat Collection

The cool guy has at least 3. One that makes a statement, one that says something about where he’s been, and one that’s just a good hat with no explanation needed. He rotates them the way other guys rotate playlists. You’ll never see the same one twice in the same week and you’ll never catch him without one when the sun’s out.

You should have:

• A trucker or baseball cap with a front panel worth reading

• One solid color, no logo, no story required

• One that’s slightly unhinged and completely on purpose

Shop Hats

The Sunglass Rotation

He has more than two pairs and he’s not sorry about it. Warm lenses for the afternoon, something thinner and more serious for the evening, a rimless option he pulls out when the mood is right. The glasses change the whole face and he knows it.

You should have:

• One warm lens, amber or orange, for daytime

• A thin metal frame that reads clean and quiet

• Something with a little more structure for when the look needs it

Shop Sunglasses

The T-Shirt Stack

This is where the personality lives. It’s not loud, it’s specific. The cool guy has enough vintage tees and graphic tops that no two weeks look the same, but they all feel like the same person. Athletic graphics, worn-in solids, the occasional football jersey worn completely sincerely. Nothing new looking. Nothing tight.

You should have:

• Two or three vintage or graphic tees that feel like they came from somewhere

• A solid heavyweight tee in a color that actually does something

• One sports-adjacent piece worn like it’s completely normal

Shop T-Shirts

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