First Date, What to Wear: A Matchmaker’s Seven-Second Rule

I’ve sat beside clients while they scrolled through hundreds of profiles and said yes or no out loud. Here’s what they were actually reacting to, and it was almost never the clothes themselves.

What to Wear on a First Date: The Short Answer

Wear something in a solid color that fits you properly, in a shape that shows your body shape in a flattering way, with shoes that look cared for. Dress one small step ABOVE whatever the venue calls for.

That’s it. Nobody has EVER fallen in love with a blazer. But plenty of good matches have died in the first ten seconds because one person looked like they hadn’t bothered to put effort into their personal presentation.

What most articles skip is that your clothes are only one of the two things being read. The other is how you carry yourself in them, and neither one saves the other.

Seven Seconds, and Clothes Are Only Half of It

Kimmy Seltzer, the confidence therapist and image coach, put a number on it when she came on the show and I’ve been repeating it ever since. First impressions used to take about thirty seconds. Now they take about SEVEN. YIKES!

Kristi Price, fifteen years into her own matchmaking practice, gave me the same seven seconds on a different episode.

Now, I’ll be straight with you about that number. The researchers who study this say the very first read happens faster still. One Princeton study put it at roughly a tenth of a second. Fine. I don’t especially care whether it’s seven seconds or a hundred milliseconds, because my point survives either way: a good chunk of this is over before you open your mouth, and you had no say in it.

Which sounds brutal, and isn’t, quite. Kristi’s follow-up matters just as much. She says she doesn’t know anyone who blew a date purely on not putting themselves together. What clothes do is set the tone for everything that comes after. They’re not the conversation. They’re the room the conversation happens in.

Nobody has ever fallen in love with a blazer. But plenty of good matches have died in the first ten seconds because one person looked like they hadn’t bothered.

Julie Ferman

And the good news, Ladies and Gentlemen, is that the other half of this is learnable. Kimmy came out of theater, including drama therapy, and she treats body language as a language of its own, something you either learned or pushed down somewhere along the way. She’s taken people who arrive with their arms crossed and their eyes on the carpet and turned them into the most magnetic person in the room. She had a former servicewoman at one of her retreats who flatly would not participate, and by the end of the weekend that woman had danced salsa, done a silly scavenger hunt in a pair of cat ears, and gone home giggling. A man came over to introduce himself at the airport on the way back. “That never happens,” she said.

So no, the answer isn’t to buy a better dress. It’s a bit of both, and the clothes are the EASY half.

What to Wear on a First Date: Women

I do something in my consultations that clients truly appreciate: I put twenty-five or thirty men’s profiles up on the screen and I watch her face while she considers them and forms an initial first impression. Do that for twenty-five years, across close to 40,000 people who’ve registered with me privately, and you learn some very unglamorous things about what actually gets a Yes.

Here’s what I see, over and over.

Wear something with a waist. The most consistent No I’ve watched women deliver on themselves is the big frumpy dress, the one where a man can’t see her waistline, he can’t determine her body type or shape. Her outfit might be comfortable, it might be trendy, new, or fashionable, but men’s eyes slide straight off it. Kimmy draws the distinction I use now: fashion is what’s current, style is what’s everlasting and cut for your particular body.

Dress for the date, not for your girlfriends. This is the one nobody wants to hear. We tend to dress for each other, ladies. For the compliment at brunch. Kimmy’s alternative has a name. She calls it a dating costume, a deliberate version of how you present that’s separate from your work self and your Saturday-errands self. Not a different personality, just a different presentation, on purpose.

Leave something to the imagination. Kristi and Cat Cantrill both landed here when I raised it with them. A very revealing first-date outfit tends to read to a relationship-minded man as a question rather than an invitation. Cat’s phrasing is the one I’ve kept: we want a little mystery, so he wants to come back and get to know her more. Kimmy’s practical version, for your dating photos: if you have one sexier picture, neutralize it with a girl-next-door shot, so a single image isn’t doing all the talking.

Watch the other extreme too. I have a client, a brilliant woman, senior in her field, who came in dressed like a banker. Brooks Brothers from the neck down, not a soft edge anywhere. Cat gave me the question I now ask both types, which is simply: let’s talk about the message you’re sending. She aims it at the woman dressed too revealingly. I aim it at the banker. Same question, opposite ends of the same street.

Kimmy told me a story that settles the whole argument. She had exactly two photos of a client to show a man. In the first she’s in severe business clothes, stiff, with a hard expression, and she’s an objectively beautiful woman. He passed. His words: “boy, she looks like she could kick my ass.” Second photo, same woman, in a dress, in the sunlight, hair loose, easy smile. Kimmy says she just heard a thump. Yes, yes, yes.

Same face, same woman, same everything! He wasn’t reacting to her LOOKS at all; he was reacting to her presence and the feeling it gave him.

What to Wear on a First Date: Men

Gentlemen, this section is shorter, because your bar is lower and you keep tripping over it anyway.

Cat Cantrill begs you, and I’m quoting her, please don’t look like you just came from Home Depot. Women read that as he didn’t think this was worth an effort, and they’re not wrong. Her prescription is not complicated:

• A button-down shirt. I’ll add the part she didn’t: ironed, and fitted through the body.
• Chinos or a decent pair of trousers.
• Good shoes. Her words are “shoes matter, gentlemen.” Kristi had a client show up to a first date in old beaten-up shoes after she’d told him not to. He didn’t get a second date, though she’s careful to say it wasn’t only the shoes. A couple of other things went sideways that evening and the shoes magnified them. Had he looked the part, she thinks the rest would probably have slid through the filters.
• Err one notch dressy. There’s a man in my world who turns up to every event I invite him to in a sport coat and a tie, and the tie is honestly a little bit over the top, and the women talk about him all night. Every single time.

One free win while I’m here. If you’re getting profile photos taken, put one of yourself in a suit. Cat only wears hers maybe four times a year and she still says do it. The point isn’t the fabric, it’s the field you’re standing in: the majority of men out there won’t put in that much extra effort, so the one who does jumps off the page. The same logic runs through my first date tips, if you want the rest of it.

The One Rule Both Sexes Get Wrong: Solids, Not Prints

Kimmy taught me this years ago and I’ve worn solid colors ever since. Patterns sit near the top of her do-not-wear list, and she gives three reasons.

1. They widen you. In a photo and in person, and they do it exactly where you least want it.
2. They shorten you. A busy pattern breaks the vertical line and you read as smaller and stockier.
3. Men don’t like them. Kimmy ran a survey on Facebook once. Same woman, two outfits, back to back, one solid and one patterned. Everybody chose the solid. Almost nobody could say why. The reason’s simple enough: they want to see the shape of the person and the pattern is standing in the way.

Want the professional proof? Watch the news tonight. They’re all in solids. That industry worked this out a long time ago.

Kristi gave me the same finding from the men’s side of her practice, without my prompting her: the big smocky things, the Hawaiian-print muumuu, the loud patterns. Guys hate patterns, she says. They want to see what her body looks like.

Dress for the Date You’re Actually Going On

Kristi’s rule is dress appropriately for the activity, and be comfortable and confident in what you’ve got on. You don’t put heels on for a hike. But “casual” is not a synonym for “whatever was on the chair.”

• Coffee or a drink. Dark jeans that fit, a solid top or shirt, nice shoes. This is the most common first date I arrange and the one people under-dress for most.
• Lunch or dinner. One layer up. A blazer, a jacket, a dress rather than separates.
• Something active — a walk or a hike or pickleball. Clean, well-fitting sports clothes are absolutely fine. Faded and shapeless are not.
• Anything at all. Cared-for shoes, hair you’ve actually looked at, and something that isn’t a print.

Not sure where you’re going? That’s a conversation, not a guess, and it’s worth having before you get dressed. If you’re still choosing the venue, my first date ideas will help. If you’re the one doing the asking, I’ve written a whole piece on asking her out in the first place that will save you some grief. And once you’re sitting down, what to actually talk about will do more for you than any jacket.

What Not to Wear on a First Date

The short list, drawn from what my clients and my colleagues actually report back:

• Anything shapeless. Baggy, tent-like, no waist.
• Loud prints. Both sexes. See above.
• Very revealing outfits, if what you want is a relationship rather than a weekend.
• Tired shoes.
• Whatever you wore to work, if work was long and hard. Kristi had a client arrive in a ponytail, and a shapeless corporate outfit, straight from the office. Not his finest evening.
• A brand-new outfit you’re not sure about. If you’re tugging at it all night, the person across the table sees the tugging.

Grooming: Beards, Heels and the Things People Argue With Me About

Beards. Kimmy and Cat land in exactly the same place, which is rare enough to be worth noting. Nobody minds a beard. EVERYBODY minds an unkempt one. Cat says the long wild unmaintained ones tell a woman you’re hiding something, and a lot of women simply won’t say yes. If you’re keeping it, groom it, and ask a couple of friends for an honest assessment of whether it suits you. Tell them to be honest. We get attached to our own faces and stop seeing them.

Hair and color, gentlemen. Gray is fine. Gray is often better than fine. What doesn’t work is the extreme, the man who’s been fully gray suddenly turning up jet black. And on hairpieces I’ll just say that bald is WAY better than a toupee, and every time I see one I want to reach across the table and toss the thing into the nearest trash can.

Heels. I’ve said for years that in 35 years of doing this I could count on one hand the number of times a man has volunteered that he loves high heels, and I’ve long suspected we wear them for the comments we get from our girlfriends. Kimmy argued with me and she won the point. It isn’t the shoe. It’s what the shoe does to your posture and your pace. You slow down, you move differently, and that’s what he’s responding to. I totally get it, and she’s right that shuffling along in flip-flops isn’t the same thing at all.

Cosmetic work. Kimmy’s answer here is the most useful thing anybody’s said to me on this subject. The procedure isn’t really the issue, the pattern is. When one thing becomes another thing becomes another thing, the question stops being should I get my lips done and becomes are my patterns working for me? Do men like the obviously fake “duck lips” ?? No. Not at all; I hear it from men every day. Ladies, please… stop it.

That thread runs through all of it. Confidence isn’t only inside work and it isn’t only outside work. Kimmy’s whole practice rests on the two being symbiotic, and I’ve watched it in my own office more times than I can count. If the outside is sorted and you still feel invisible, how to be irresistible to men covers the rest of it — and if the inside is where you’re stuck, I’ve written about the confidence underneath it separately.

When It Goes Wrong Before You Even Arrive

My favorite story on this subject is Kristi’s, and it’s the one to hold onto if you’re anxious.

A woman got stuck in appalling traffic on the way to a first date. She worked in a hospital, in physical therapy, and there was no chance of changing. She was arriving in scrubs. She called and told him so. He said: I’ve reserved the table, you can show up in your scrubs, I’d be happy to see you.

They married.

Thirty seconds of honesty about a mess. Thirty, not five minutes, and that’s a rule I give every client. Then straight back into the evening. That isn’t a wardrobe skill. That’s emotional steadiness, and it’s the most attractive thing at any table.

Look, I’ve been at this since 1990, and if there’s one thing I’d take off your shoulders it’s the idea that any of this has to be expensive. During the lockdowns I orchestrated hundreds of park bench dates, and I still do, because a bench and a coffee and two people who actually want to know each other beats a pricey tasting menu every time. One of my dear friends is married to a man who is “so tight he squeaks” and he’s never once bought her a diamond – but she says he has been picking up the bills for dental emergencies and roofing invoices consistently, without a word about it. She’s the one who pays for the fancy hotels, because life is too short for the Travelodge, and yet she says he’s happy at the Travelodge. They’ve been sorting these things out cheerfully for thirty-three years. Choose your outfits carefully, don’t sweat the little things and look for what’s right, vs. what might be missing.

FAQs About What to Wear on a First Date

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