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…