It’s especially hard to date when it’s cold, but conjuring a series of winter date night outfits can be just as overwhelming as decoding your relationship status—let alone triangulating the best spot to go for dinner on a chilly February evening. (Or lite bites. Or drinks. Are we better as friends?!)
We can’t help you puzzle through your situationship or what to do on your next date. But we can help you suss out what to wear when the big night finally arrives. Whether you’re meeting a total stranger for a quick drink, trying to convert a fall fling into a main squeeze, or just keeping the spark alive with your ride or die, you’ll want to dress right for the occasion. That Valentine’s Day lands smack in the middle of winter doesn’t make things easier; book those reservations now, fellas.
Consider us your sartorial wingmen, then, because we laid out a handful of foolproof winter date night outfits for every type of cold-weather link-up in the books. Learn them, live them, love them—but maybe give them your own twist, too, lest your date read this article and wisen up to the source of your newfound drip.
The Vibey Wine Bar
It’s debatable, but perhaps the most versatile date spot is an intimate bar. And unless you know you’re going to a lowkey dive, we’d stick with an outfit that’s equal parts casual, dressed-up, and sexy. It may be freezing, but leave the puffer at home and opt for a bomber jacket or a wool topcoat. Layer it with something like a button-up or a polo cardigan, because a top with a few buttons undone is flirty but not too forward. For the lower half, a pair of deftly-cut trousers with a higher waist to sync up with that bomber jacket and finish it off with a pair of slick boots. Very Austin Butler-coded.
The Dinner In
Going out on a date doesn’t have to mean going out. With a few candles, some flowers, and a delicious home-cooked meal, you can set the mood right from your own abode. It’s your house, but don’t go cheffing it up in your couch potato outfit. A denim western shirt is a great option here. It’s got a rugged allure that says you work with your hands (hey, Ina Garten’s chambray shirts aren’t too far off). You can roll your sleeves up when you’re at the stove, or leave it off until you’re ready to set the table. It’s easy to snap on, but way easier—and more fun—to snap off. As for the rest of the outfit, a slick white tee will give Carmy while some a pair of clean, pressed trousers will give Stanley Tucci, especially if you’re cooking Italian. Not a bad combo. As for the shoes, that really depends on whether you’re a shoes-off house or not.
The Light Bites
You’re not meeting up at a place that only takes reservations. Maybe it’s a burger joint or a tapas bar. Or maybe it’s the old delicatessen before catching a movie. Showing up in a suit to chow on a wet pastrami sandwich can come off as forceful, out of place, or even intimidating. Relax, bud! You’re scaring the hos! Try a thick wool sweater over a button-up shirt and your best-fitting, washed out jeans. Sneakers? Sure, as long as they’re not candy-coated, hypebeast kicks. Stick to a more subdued or even minimalist pair of sneakers like Converse or any of the Samba alternatives. And if you haven’t guessed it by now, we’re just ripping Billy Crystal’s outfit from When Harry Met Sally.
The White-Tablecloth Reservation
Gearing up to dine at an exclusive omakase joint or at a Michelin-starred restaurant with a months-long wait list is no time for jeans. These hoity-toity establishments will require a jacket, and by jacket, they mean a blazer. And you don’t want to be the guy who has to borrow one from the restaurant. So lean into tailoring and have fun with really getting dressed up because that’s part of the fun anyway. Don’t mess around trying to pair an odd jacket with contrasting pants. Opt for the full suit with a dress shirt and a tie. Too many bozos are out here trying to go sans tie and end up looking like a finance bro who just discovered menswear from 2015. Toss a handsome topcoat over the look for the lead up to the restaurant and you’re good to go.
The Weekend Gallery Hop
Think big dramatic topcoat over a sportcoat, cashmere sweater, vintage jeans, and loafers, or even bigger more dramatic topcoat over a turtleneck, pleated trousers and moccasins. The idea is to play the charming ‘90s heartthrob, the kind of dude who appreciates the arts.
The Late-Night (or Early-Morning) Boogie
If you’re following up your tasty dinner with some rug-cutting, you’ll want to wear something fun. This is when you bring your out going-out shirt, your dancing shoes and your best moves. Opt for a slinky shirt with a liquid-y drape and maybe a bold pattern, something you might have worn to Studio 54 if you were around then. For your dancing shoes, a pair of swanky loafers, gussied up derbies, or even cowboy boots will do as long as they have a heel. You won’t want to be wearing a sweater on the dance floor, so leave the extra layers at the coat check along with your inhibitions (and remember to bring cash).