How to Dress on a First Date, Four Tips for Every Guy

Yeah, yeah, we get it — first dates aren’t easy. Navigating intimate one-on-one social interactions can be intimidating. And your choice of outfit is just one more factor that can get in the way of a great first date. It shouldn’t be.

Regardless of whether you met on an app or IRL, what you wear to your initial date ultimately is not the defining factor in determining potential future dates. That decision comes down to you. Here are some steps to help you decide what to wear so you can let your best self shine on the first date.

Figure out the Details

Before you open up your closet, figure out the details of the date. Are you meeting for drinks at a dive bar? A stroll through the farmer’s market? Are you headed to a concert for that artist that you both love? Is that artist Philip Glass? All these questions play into what pieces you’ll pull from your closet. Like any event, you dress for the occasion, whether that means headed to the office or headed to that Halloween party. The first date is no different.

This should be obvious, but check the weather. Nobody wants to get caught in the rain, especially on their way to a date. Then, gauge how formal or casual the situation will be.

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Dress Comfortably

You want to give your date your full attention. Wear something that makes you comfortable, both physically and mentally. Once you’ve got that nailed, you’ll begin to feel more confident.

Try wearing your favorite outfit. If you don’t have one, start with your favorite pair of pants and work from there. The worst thing you can do is pick shoes that are too tight or a cashmere sweater that looks good for five minutes before you start sweating through it. Those problems will take your focus away from where it really matters.

As long as you feel good in your own clothes, that’s one less thing you have to worry about when the time comes to actually get to know each other. If you still can’t put something together that you’re satisfied with, the next step should help.

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Be Yourself

Whether you’ve found a favorite outfit or not, pick one that’s a good representation of you on a normal day. Don’t show up to the date dressed in an outfit you’d never wear in any other context. The first date is all about getting to know each other, but that won’t happen if you’re dressed like someone else. If that means sweatpants and sneakers, so be it. If that means a blazer and tie, fine. A person who’s gonna judge you based on your clothes rather than your character is probably not someone you want to be around, romantically or platonically.

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Ignore the Bullshit

There’s no shortage of advice that tells you what clothes to actually wear on a first date. But a lot of it really misses the point of a first date. No, wearing red won’t get you laid. No, don’t go out and buy something new just for the date. But yes, probably don’t go crazy on cologne.

If you haven’t noticed by now, there’s no concrete piece of clothing we’re telling you to wear. You can express a lot about yourself through your style. But remember that your clothes are not you. They may indicate what you like, but you will ultimately be the one talking, not your jacket.

And besides, you’ve already agreed to go on a first date — there was as a mutual attraction to begin with.

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