How To Pick A Great First Date Outfit For Men: The Definitive Guide 2023

Updated: February 3, 2023

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).

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.

2. 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.

3. 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.

4. 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?”

5. 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.


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