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.
6 Key Elements to an Excellent Date Night Outfit
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, handsome pair of black derbies 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.