5 Date Night Outfits for Men Guaranteed to Impress in 2025

So you’ve got a date. You ol’ dog, you—congrats! Figured out where you’re going and what you’re doing? Now comes the tricky part: what to wear. Date night outfits, whether you’ve locked in a coveted Saturday night reservation or planned a low-key night in, are pretty simple: they should help you look your best, all without looking like you tried too hard.

If you’re at the starting line of the courtship, aim to look cool and put-together, but still like you. Comfortable, well-fitting basics that don’t shout tend to work best. Win them over with your personality and your jokes, not the big logos on your sweater. The key is to look like you’ve put in some real effort, without expecting your clothes to do the hard work for you. And, yes, the old adage holds up—people really do clock your shoes first, so make sure you’re not wearing anything totally cooked. Layers are always smart, too, in case things move from dinner to a walk or a nightcap.

This isn’t just sage advice for the early stages. If you’ve been with your partner for a while, it’s worth keeping things interesting. Dressing up a little for a night out shows that you still care—trust me, they’ll appreciate it. To get you inspired, we’ve put together five date night outfits for every kind of scenario you might encounter out there, and explained how to dial it in for each one. Good luck out there, stud.

The Leisurely Daytime Link-Up

The daytime hang is the most casual of dates. It’s a simple temperature check, but that doesn’t mean you can wear your sweats. Maybe it’s coffee, maybe it’s going for a walk, but it’s fall, you’re wearing a sweater, you’re basically Billy Crystal in When Harry Met Sally. The goal is to look casually put-together—show them you have your life in order. (Bonus points if you bring a dog, ideally your own.) Here, there are a couple of ways to make an impression: a cool jacket, and a sturdy pair of boots to give you an extra inch of confidence. If they like the fit—and you don’t say anything stupid—you might just earn yourself a date upgrade to drinks or dinner.

The Weekend Culture Vulture

So you’ve decided you like each other enough for a multi-hour activity. Nice! Maybe it’s a Picasso-peeping museum visit, maybe it’s a concert in the park. Either way, you want to feel comfortable and relaxed, but still keep things versatile, in case the date goes extra innings and those wholesome daytime plans roll into a cheeky evening cocktail or night on the town.

An Oxford-and-sweater combo with dark denim says, I made an effort, while a leather jacket adds just the right edge—and gives you something to offer if they get chilly. A clean pair of dark sneakers works fine, but expertly-made, exceptionally-comfortable Chelsea boots take things up a notch. Plus, they’ll keep your dogs from barking if the date goes the distance.

The Post-Work Drinks

You’ve just clocked out and it’s straight from the office to your date. If you’re coming from somewhere with a dress code, well, that's what you'll be wearing. (Though we'd say ditch the tie, swap it for a merino knit, and call it a strategic rebrand.) But if your office leans casual, or your office is at home, bring the cool.

A light jacket layered over a graphic tee, with well-cut jeans or chinos and a solid pair of boots will do the trick. A top-notch leather boot like this from Tecovas is cool enough for a bar, relaxed enough for dinner, and versatile enough that you won’t feel overdressed if plans shift. They’re also a welcome upgrade from sneakers that won’t have you selling out to lace-ups. And don’t skip the scent. A long-lasting fragrance goes a long way; let some of it do the talking when you order another round.

The Table-for-Two

Whether it’s a third-date dinner or a romantic evening out with your long-time partner, it’s worth putting in the extra effort. Dressing up a little signals that the night means something—even if it’s just at a cozy spot around the corner. And sure, the restaurant is no jacket required, but it never hurts to throw one on. You’re not going full suit-and-tie here—just a sharp jacket over a knit. It gives a sense of polish without feeling stiff.