What Your Clothes Are Actually Saying

How she reads you, garment by garment

You already know your clothes talk. Here's the part you can't hear: what they're saying, and to whom. None of these is wrong. They're just choices that communicate — and when you're hoping to be chosen, it pays to choose on purpose.

And she hears it twice: first in your photos, then across the table. The photo makes a promise; the date is where she checks it. So you want clothes that say the same thing both times.

Let's build it the way you get dressed: from the ground up.

Shoes: the tell you didn't know you were giving

Start at the bottom, because this is the most revealing thing you own and you have no idea. There's actual research on this — shown a photo of a stranger's most-worn shoes, people can make a decent guess at his age, his income, even how anxious he tends to be in relationships.

Shoes are also where the two reads split. In a full-length photo they're maybe 5% of the frame, and more often than not they're cropped out entirely. On the date, they're right there. They pull the whole outfit together, so they're worth your attention even when the camera isn't looking.

Clean minimal sneakers — the easy win, and they've been in style so long you probably already own a pair. Reads as active but not gym-obsessed, put-together but not fussy. You're a good guy who'll walk her home. Hard to get wrong, which is exactly why it's safe.

Dress shoes — a man with a sense of himself who wanted to look like a competent adult. Great, if the occasion earns it. On a casual date they can read as trying to be taken seriously, which is a different thing from being serious.

Boots — capable, and not precious about it. You own a toolbox; you'll know what to do when the sink backs up. Rugged without shouting about it.

Running shoes, worn as everyday shoes — the "I find most shoes uncomfortable" look. Says comfort was the only thing you were optimizing for, and not her comfort. Yours.

Pants: darker than you think

The least dramatic category, so it's the easiest one to get slightly wrong without noticing.

Dark jeans or a dark chino — navy, charcoal, black. Reads as deliberate, photographs cleaner, and does more for you than the light-tan chinos most men default to without deciding anything. Slim or athletic cut if you're built for it; the fit matters.

Light/khaki chino — not wrong, but it walks a line. Pleated and baggy, it's Casual Friday, 1996. Slim, flat-front, a little broken in, it's a man who knows exactly what he's doing in khakis. A decision, not a default.

Sweatpants / athleisure — I know you'd live in them if you could. On a date or in a photo, they read as I didn't expect this to go anywhere. Wear pants with a real waistband.

T-shirts: what you do with a plain tee

The t-shirt is a purity test, because there's nowhere to hide — it's just fabric and fit and whatever you've decided it should say.

The plain, well-cut tee — quiet confidence. It lets you be the thing she's looking at instead of your shirt. In good fabric — the kind that feels smooth, not papery — it genuinely looks great, layered or alone. It's the counterintuitive place where spending real money actually shows. Not tight, not a tent. Cut to your shape.

The clever graphic tee — you're outsourcing your personality to a joke on your chest. Sometimes it lands. More often it reads as needing the shirt to break the ice, and now she's evaluating the joke instead of you.

The old concert tee — careful here. It feels like this is who I am — what you want to say — and reads like this is who I was. It quietly clings to a version of you from a better summer a while ago. Save it for date eight, when it's endearing instead of load-bearing.

Sweaters: lead with feel

This is the category where material makes the argument for you, so let it.

Cashmere — the please keep touching me garment. In a photo it reads as soft; in person it proves it. When she puts a hand on your arm, you want oh, that's soft — and you want the hand to stay. Own one that fits and you're most of the way there.

A chunky knit — warmer, more texture, more character; reads cozy and a little deliberate. Great in fall. Just make sure it fits your frame instead of swallowing it.

The quarter-zip — the office uniform. It says comfortable at my desk. Not offensive — just the easiest thing in your closet to forget, and that's its own problem when the whole game is being remembered.

The jacket: the loudest thing you'll wear

This is where the outfit starts making a thesis statement. Pick the one that sends the message you mean, because the wrong one looks borrowed faster than anything else you own.

The suit jacket — you reached for it because it's the nicest thing in the closet. But a sharp, structured shoulder reads as all business, in a profile photo or across a dinner table — like you're heading to a deposition. Which works if you're the attorney, and authority is the first thing you want her to see. If that's the aim, wear the whole suit, trousers and all. What doesn't work is the orphan: a suit jacket pulled off its pants and passed off as a sport coat over jeans. They look awfully similar. They aren't the same garment, and the mismatch shows even to people who couldn't tell you why.

The soft-shoulder / chore coat / unstructured blazer — I made an effort, and I'm not making a big deal of it. Relaxed shoulder, over a tee and jeans, and you look put-together and completely at ease. This is the one that works on almost everyone.

The leather jacket — edge, a little confidence, a man with a self-image. Not wrong — it's specific. It pulls toward the woman who wants that energy and away from the one who doesn't, which is the whole point of a signal. The only real failure is wearing one that isn't yours. Leather on a man it doesn't belong to reads as a costume from across the room.

The bomber — current, unfussy. Says less than the leather and risks less, which is either a relief or a missed chance, depending on what you were hoping for. Watch the fabric: shiny nylon dates you; suede or a matte cotton doesn't.

Outerwear: the city-or-mountain question

The seasonal last layer — it's in your cold-weather photos, and it's the first thing she sees when you walk in. It answers a question she didn't ask out loud: are you dressed for people, or for weather?

A proper wool coat — the grown-up read. Urbane, considered, a man who knows he lives in a city full of other people and dressed accordingly. The biggest upgrade most men skip.

A technical outdoor shell — practical, prepared, a little outdoorsy — but on a date it can read as dressed for a summit I'm not currently climbing. Right on the trail; an odd choice for dinner, or for a photo.

The heavy down parka — warm, honest, and genuinely necessary in a real winter, but it reads younger and more casual. In a deep freeze, nobody's judging. Over a t-shirt on a 50-degree day, it's a choice — and she'll read it as one.

The one universal

Whatever you pick, beat-up and dirty overrides all of it. Scuffed shoes, a pilled sweater, a collar that's given up. The camera catches more of this than you'd think, and she catches the rest. It doesn't read as casual — it reads as this man overlooks things. And she will wonder what else.

Nothing here is a rule. It's a decoder. Pick the one that says what you actually mean.

Which picture should I open my online dating profile with?

You do not have six images to make an impression. Rather you have ONE image to maker her curious and five chances to undo the good you've done. The order in which you organize your images for your online dating profile is critical to your success.

Always open with an image where you are looking at the camera and smiling. Eye contacts and smiles. The tried and true way to calm the animal instinct in us and telegraph trust worthiness. Do not wear sunglasses in this first one. It's essential your eyes are visible.

Picture two in the line up should echo the same sentiment as picture one, trust values. Or else she could be wondering if its a fluke and never to be had again. Women loves consistency.

Picture three, four and five. Here is where you have room to play. You've established trust and that you are a good guy, now let's find something that is interesting or a potential conversation starter.

Things to watch out for here in pictures three, four and five:

1. Group photos with more than 4 people. It's wasted real estate. She doesn't need to be picking you out of a lineup.

2. Group photos with someone of the opposite who is younger than your grandparents. It doesn't matter that is your twin sister. The women looking at your profile doesn't know that and the first question that pops into her head is, "Is that his ex?"

3. Anything that has been ridiculed online: sunrise at Machu Picchu, petting tigers in Thailand, holding a 15lb fresh caught salmon. You are trying to show something interesting about you, hobbies and travel, except so many have done exactly the same and the Internet has taken to mock. It's sad. But you don't want to appear to not be in the know so let's save those memories for date 8 when you are cuddled up in bed and scrolling through each other's Instagram account.

Picture six, the closer. You've taken great pains to construct a portfolio of your best self, the mistake would be wanting to cram in just a little bit more info. No. No. No. Instead, let's reinforce what she has learned about you thus far --- and the most important thing, that you are a good guy. Close out your profile with another trust establishing photo where you are all eye contacts and smiles.

Everything else about you...we save that for the date.

What should I wear in my dating profile?

(updated 2026)

I get some version of this question before almost every session: What should I wear?

You already sense the answer matters — that's why you're asking. You know your clothes are saying something. You just can't tell what, or to whom.

I've been photographing men for their dating profiles for a decade. Before that, a decade-plus as a fashion and advertising photographer — and many years as a woman looking for love, on the receiving end of every choice men made. I've watched a lot of guys dress for what they think a woman wants and miss. Not out of apathy. Because nobody ever taught them the clothes were talking the whole time.

So let's start with where you're actually going.

Dress for the date, not the camera

The mistake is dressing for the photo. Dress instead for the thing the photo is supposed to get you — a first date, on a good day, in this city.

The register I'd aim for is weekend brunch. Not because you're going to brunch, but because it's the one dress code that's put-together but relaxed. Nobody's in a suit; nobody's in sweatpants. You look like you gave it a thought and then stopped thinking about it. Hit that note and you're right for coffee, for afterwork drinks, for almost anything a first date in New York turns out to be.

The whole game: cut and material

Two things carry menswear — the cut and the materials.

A plain t-shirt in excellent cotton, cut close enough to read your actual shape, beats anything with a logo, a pattern, or a statement stitched into it. Here's why it works: picture a woman putting her hand on your arm. In that half-second you want oh, that's soft — and you want her to leave her hand there. That's the whole thing. You're being looked at from across the room, sure. But you're also, hopefully, going to be touched — and most men dress only for the first and forget the second.

Fit tells her you've got it together. Material tells her you're worth getting closer to. The rest is noise.

Tops: lead with feel

Cashmere is the easy win — it does the please keep touching me work for you. A good cashmere sweater or a lightweight cashmere polo reads as effort you're not announcing, which is exactly the right amount of effort. Own one that fits.

Somewhere like Vince is a fine place to feel what soft cashmere is supposed to feel like without a second mortgage — and if your budget runs to Loro Piana, you already know where to look. The label isn't the point; the fact that she wants to keep caressing you is.

One caution: a plain t-shirt in a good fabric, from a Sunspel or a Buck Mason, genuinely looks better than a cheap one and does the work without a layer over it. I know it feels absurd to spend real money on a t-shirt, but having photographed endless men in plain t-shirts, I can tell you real quality is visible. Solid colors. No patterns. Let the fabric talk.

The jacket: pick the one that's actually you

A jacket is the loudest thing you'll wear, so it's worth knowing what each kind says before you run out the door.

The common mistake is grabbing a suit jacket because "dressed up" feels like you are a "serious" person. A sharp, structured shoulder can work — but as they say, you need to wear the suit and not let the suit wear you.

A soft-shoulder or unstructured jacket — seersucker in summer, an unlined blazer, a chore coat in fall — is the safest read there is: I made an effort I'm not making a big deal of. Over a tee and jeans, you look put-together and completely at ease, which is the exact combination you're after.

A leather jacket says something sharper — edge, a little confidence, a man with a self-image. That's not wrong; it's specific. It pulls toward the woman who wants that energy and away from the one who doesn't. The only real failure is if it's a costume and not you being you. Wear it only if it's already YOU.

A bomber is the easy, current, unfussy option. It says less than the leather and risks less — which makes it either safe or forgettable, depending on what you're going for. But here materials really matter: a shiny fabric will channel the '80s, whereas suede can call forth an I'm-ready-for-Paris-Fashion-Week vibe.

Pick by what you want it to say.

The hoodie: it depends entirely on how you wear it

Worth its own note, because it's the piece men get most wrong without knowing it.

Reached for by default — because I said "Sunday brunch" and it's the soft thing you grab that's comfortable and asks nothing of you — a hoodie tells a woman I haven't quite decided to show up for you, this is just a drive-by.

But a good hoodie — well-cut, no faded gym logo — worn on purpose, layered under a jacket, can flip the read entirely: I'm at ease in my own skin and I'm not performing for you. Same garment, opposite message. The difference is whether it's a choice or a reflex.

Pants: go dark

You have a few categories of options: jeans, chinos, and khakis. You might be thinking to yourself, but there's also sweatpants, or athleisure, and I would totally wear those to a weekend brunch. Here's my advice: save that until after you've been naked with the other person. Until then, think "pants without an elastic waist."

For ease, I'd steer you toward jeans or chinos. Believe it or not, there's actually a difference between the two. To keep it simple: chinos don't have pleats in the front, khakis can. You don't want pleats unless you're actively cosplaying '90s nostalgia. In terms of color, go darker — navy, black, or even gray. It reads as more deliberate and photographs cleaner.

A bit of trivia, since you're now paying attention to these things: chinos got their name from a nineteenth-century supply chain. The twill they were cut from was milled in China, so Spanish-speaking soldiers who were issued the trousers simply called them chinos — "Chinese." The name stuck, the fabric became standard American-issue kit, and the pants have been in rotation for well over a century. You're wearing a small piece of logistics history.

For fit, slim or athletic off the rack usually works if you're built that way. J.Crew and Banana Republic produce a wide range and are solid utilitarian choices. The cut here is what matters; make sure your butt looks good in it, because the ladies will be looking. Two pairs is plenty for a photoshoot.

Shorts: usually not, and here's why

Knobby knees are an aphrodisiac for a very select few. Beyond that: shorts pull the whole read toward didn't think about it, and they're the hardest thing in menswear to get right — the length, the shoe, the proportion. It's where most men look like they got dressed in the dark.

The exception: if your life is genuinely warm-weather and casual and you want photos that are honest about who you are, one considered warm-weather look can be honest rather than lazy. But that's a decision, not a default.

Shoes

Shoes need to go with the outfit, and that's about all the worry they deserve. Casual weekend brunch? Sneakers and clean running shoes are totally acceptable. If you've suited up, then yes, bring dress shoes to match. The thing to remember is that in a photo your shoe is about 5% of the frame. It's likely to get cropped out entirely — and if the person on the other side of the screen is studying your shoes, something has already gone wrong.

What you're actually doing when you get dressed

Every piece you put on is sending a message before you've uttered your name. Not a style grade — a read on who you are. The light khaki and the dark jean aren't better-or-worse; they're two different sentences about the man wearing them. The hoodie and the cashmere aren't casual-versus-dressy; they're two different things to tell a woman about how much you've shown up for her.

You're transmitting all of it, all the time. The catch is that you can't hear your own signal — but she can. She's receiving it perfectly clearly, which means it's easy to broadcast one thing while hoping for a response to another. That's not a taste problem. It's a translation problem, and it's the real reason the right clothes matter: not to look better, but to say the thing you actually mean.

This isn't about dressing to win. It's about being read the way you'd want to be read — and letting the photos show an accurate portrait of you.

Need a taxonomy of what your clothes are saying? Read on…

Online Dating Profile - DOs and DON'Ts

Even though you have approximately 6 images in your online dating profile, you do not have 6 chances make your case and get a swipe right. You have one, maybe two images to get it right, the rest is there to reinforce the opening message. In another words, you have four more chances to reinforce why they should go out on a date with you or you four more images to f*ck it up. Choose wisely. 

You DO NOT need to convey EVERYTHING about you in these 6 images. 

You DO NOT need a guitar in one hand and a puppy in another. If you do play and own a dog, that is great! But only include them in the photos if it makes sense (and real) — or else it’s just silly and will prompt questions you can’t answer on the date. 

The first and most important thing you need to get across in your online dating profile is that you are trust worthy. Eye contact and a real smile increases a right swipe by 21%. DO SMILE. LOOK IN THE LENS - MAKE EYE CONTACT. Your date needs to know that you are not a serial killer. 

Which is why, you SHOULD NOT open your profile with an image of you wearing sunglasses. Leave that image towards the number 4-5 slot. 

Shirt-less photos is everyone’s favorite topic. Do I/ Don’t I?
From the ladies perspective, it is an overwhelming NO. It telegraphs cheap and easy. That also holds true for images of women scantily clad or in tiny bikinis. The temptation is strong, you work so hard on your bod, going to the gym 6-days a week, you want to get some credit for the 6-pack. The credit will come later, in the bedroom. 

Mirrored Selfies is another big NO NO. Bumble banned it from the app. Isn’t that proof enough that it’s a bad idea? 

DO NOT include large group photo where it is difficult to tell which one of the 12 bridesmaid/ grooms men you are. You might look like a million bucks that day but it is just confusing. 

DO NOT include more than one images of you holding a drink. It prompts the question of either being into parties or potentially an alcoholic. 

DO NOT crop the image in such a way that it is clear you cut someone out of the photo. It makes the other person wonder, who is that? Could that be their ex? Even if the other person in the photo is your sibling, it doesn’t matter. You don’t want the question in their mind in the first place. 

DO NOT include photos of you with someone of the opposite sex. Again, you don’t want the question in their mind. 

DO NOT blur out the other people in the same photograph. It looks creepy first of all. Secondly, it’s sloppy.

DO include a photo of you looking away, off camera. We are looking for an unguarded moment where you look real and engaged. For men, images looking away and off camera has an increase in swipes. 

DO consider something that shows off the other parts of your personality. A goofy and funny image added levity to overall profile. It telegraphs that you don’t take yourself too seriously and are secure enough to put it out there. 

Most people turn the written portion of their online profile into a narrative version of their LInkedIn profile. “I do this for work. I love to run. Foodie. Love to travel and have lived in X,Y, Z places.” That is all great, except what you have constructed is a closed loop. There is no way in for the person on the other side of your profile. What could their opening line be other than…”So, how long did you live in Bogata?” “Wow! I’m a foodie too!” It’s hard to gain traction. 

DO end your profile with an ask, a call to action. Ask a question. Extend an invite. Make it easier for them to engage in a fun conversation with you. Create a more optimal situation for their interest to turn into a fun conversation, into a date.