How To Pick A Great First Date Outfit For Men: The Definitive Guide

What’s the best first date outfit for a dude? It depends on who you’re asking. Some women love a man in a suit, while others go crazy for a guy in grey sweatpants—but neither of these are probably things you want to (or should) wear to grab a coffee on a first date. So here’s a definitive guide on how to pick a first date outfit for men who want to look good. 

You don’t want to pull a Ross Geller and wear a “cool” pair of leather pants on a date, only to end up in the bathroom sweating and with some form of diaper rash. The good news is, once you figure out one or two go-to outfits, you can repeat these for all of your first dates (hopefully there won’t be too many before you meet someone special—but it’s always better to be prepared). 

An expert’s tips to pick out the perfect first date outfit for men

  1. K.I.S.S. – Keep it simple, stupid

I’ve said this before and I’ll say it again, I think the sexiest outfit a guy can wear is a fitted white t-shirt, a pair of slim-fit black jeans, and Chuck Taylor’s. Or maybe a black fitted t-shirt, and a pair of well-fitting blue jeans. Either way, I think you can guess that I like guys in something simple and fitted—and I think most women would agree. 

Of course, if your style is more about kitschy patterned button-ups and neon striped sneakers, don’t tone it down to impress a date. But if your style is normally simple, now is not the time to try to be the male Lady Gaga. If a t-shirt feels too basic, try a Henley or a raglan-sleeve tee.

Also, keep in mind that fit is everything. Invest in shirts and pants that really fit you well. If you can’t find clothes that fit you well, do some research and get some things tailored. I promise you it’s worth it. Ever wonder why celebrities look so good even in basic outfits? It’s because everything is tailored exactly for their body type, and doing that with just a few outfits doesn’t have to be expensive.

Some things I recommend avoiding in most cases: sweatpants, sandals, shorts, scarves, tank tops, and anything you’re not super comfortable in. 

  1. Don’t be afraid to put out some feelers

Here’s an idea. Instead of asking your usual, “margarita Monday or taco Tuesday?” ice-breaker, why not ask your latest match if she prefers guys in suits or sweatpants. If you’ve ever had a serious girlfriend, you probably know that many women love playing stylist for the men in their lives. Use that to your advantage to find out what your date is into when it comes to men’s style. She may not have a preference, but it could also reassure you that your decision to wear your favorite vintage jean jacket is a good decision.

One time, a guy I had first date dinner plans with told me over text that he’d be coming straight from the office, so he’d be wearing a suit, but that he didn’t expect me to be as dressed up. This warning allowed me to know that just because he’s wearing a suit tonight, that doesn’t mean he’s the type of guy who wears a suit to every dinner outing. It also let me know that if I wanted to dress up, I wouldn’t feel overdressed, but that he wouldn’t judge me if I wasn’t dressed as fancy as he was. As a woman, let me tell you: we appreciate these things! 

  1. When in doubt, ask a female friend

If you feel weird bringing up fashion with your latest Bumble match, see if you can ask a female friend for her opinion on your go-to first date outfits. Like I mentioned above, some women love to play stylist, especially when so many guys seem a little challenged in the wardrobe department. Just like you’ve helped your best girl-friend build her Ikea furniture, she can help you pick out the right jeans at Uniqlo. 

  1. You don’t want your date to remember you for your outfit

This tip may sound a bit controversial, but hear me out.

Do you really want your date to remember you as, “the guy with the puka shell necklace” or “the guy with the purple sweater?” Wouldn’t you rather her remember you as “the really passionate architect” or “the guy who kept her laughing through an entire three-course meal?”

I recently went on a first date with a guy who wore a Citizen Cope t-shirt and a leather jacket. While it was a totally fine date, the most memorable part about it was his t-shirt and me wondering if I should comment on it or not. Of course, if it was a band I loved, I would have. But I only know a few Citizen Cope songs, and something about it sort of made me feel like he was trying too hard or something. It’s definitely an unfair judgment on my part, but it is what it is and it’s something to think about.  

  1. If it’s not broken, don’t fix it

As I mentioned above, you do not need 20 great first date outfits. You need one or two, maybe five max. And, you can always buy the same first date outfit in different colors. That’s the beauty of being a guy and keeping it simple, nobody is going to remember that black t-shirt and jean combo and realize you’ve worn it three Tuesday’s in a row. 

At the end of the day, you want to be yourself, but the best version of yourself (at least for a first date). The version that shows up to brunch with your grandma, not the version that wakes up in pizza-stained sweatpants on a Sunday morning. I hope these tips for choosing a great first date outfit for men can help boost your confidence, enjoy great first dates and many more second dates

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