There’s enough to worry about when headed into a date in the winter—What if you slip on ice? What if your car gets plowed in while at dinner?!—you don’t need to stress about your outfit, too.
That’s why Style Girlfriend put together the ultimate guide to date night outfits for guys in the winter.
Looking for date outfit ideas for another season?
After all, helping guys get dressed to look and feel their best is, like, kind of our whole thing?
So, here we go!
What to know about men’s winter date outfits
First, consider what you’re doing.
Is it day date winter outfits you need? Nighttime looks? A casual evening out at the movies, or a stroll through a snow-filled park? An ugly holiday sweater party?
Once you’ve got the occasion locked in, think about what you feel like a million bucks wearing. Because confidence is always the best look.
To help with outfit ideation, we’ve pulled together date night outfit ideas for men that work for all of the above.
…Except the ugly holiday sweater party.
You’re on your own there.
Here’s what you’ll find in this guide to winter date outfits:
- 8 winter date night outfits for guys you can shop right from this guide
- helpful tips on getting ready for a winter date
Below, 14 men’s winter date night outfits:
Winter Date Night Outfit #1
The Look: Drinks at your favorite spot
SG Says: Looking your best should mean feeling your best, too. If that means a simple striped sweater and dark jeans, great!
Swap the sneakers for a pair of penny loafers to give your outfit a slightly special vibe. If it’s warm enough out, skip the socks and cuff the jeans to flash some sexy ankle.
Winter Date Night Outfit #2
Shop the outfit:
- corduroy drawstring pants: Katin
- denim shirt: Billy Reid
- clogs: Birkenstock
The Look: Indie music artist vibes
SG Says: The pants are drawstring and the shoes are slip-on. Could this date night look be any easier (or more stylish) to slip into!?
Winter Date Night Outfit #3
Shop the outfit:
- plaid overshirt: Wax London
- t-shirt: Todd Snyder
- pants: Billy Reid
- boots: Rancourt & Co for Huckberry
The Look: Lumberjack in the city
SG Says: Don’t sleep on a shirt jacket (or “shacket”) as a go-to layer in cold weather.
It gives off a cozy, burly man vibe that definitely lends itself to in-booth cuddling on your next winter date.
Winter Date Night Outfit #4
Shop the outfit:
- flannel shirt: L.L. Bean
- t-shirt: Buck Mason
- boots: Blundstone
The Look: Casual winter cool
SG Says: This date night outfit would be perfect for outdoor activities. Just don’t forget your jacket.
Winter Date Night Outfit #5
Shop the outfit:
- polo sweater: Buck Mason
- flat-front trousers: Billy Reid
- sneakers: Autry
The Look: Dressy casual
SG Says: If you want to dress up without feeling stuffy, like for an outfit to wear on a dinner date, this is the perfect look.
Flat-front twill pants with a polo sweater in a winter-y neutral and elevated sneakers.
Winter Date Night Outfit #6
Shop the outfit:
- plaid shirt: Corridor
- corduroy pants: Marine Layer
- boots: Clarks
The Look: Easy elegance
SG Says: Our whole team loves this Corridor plaid shirt. It gives the wearer an elevated vibe without working too hard at it.
It’s a great date night outfit for guys to wear to a bar or casual restaurant.
Winter Date Night Outfit #7
Shop the outfit:
- rugby shirt: Abercrombie & Fitch
- workwear pants: Madewell
- sneakers: Nike
The Look: Gen Z-ready
SG Says: This look may not work for those over 35, but if you were born after 9/11, this might just be the perfect winter date night outfit.
Sorry not sorry! The youths will take over the earth, might as well cede some (style) ground now.
Winter Date Night Outfit #8
Shop the outfit:
The Look: Casual sophistication
SG Says: When it comes to date night outfit for guys, opting for a turtleneck is a pro move.
Truly, no list of can’t-miss winter date night outfits would be incomplete without at least one turtleneck.
This look looks effortlessly cool, with “hip” sneakers and black jeans to keep the overall effect laid-back.
More winter date outfit inspiration…
Before you go!
Check out 6 #SGapproved pre-date tips below…
1. Change before the date
When you’ve got a date in the winter, it’s a good idea to carve out time to leave your work brain at the office and your daytime outfit in the hamper at home before a big date.
Because we’ll give it you straight: Rolling up to a winter date in wet boots you’ve been stomping around in all day, a bad attitude from a meeting that should have been an email, or a fresh-from-lunch stain on your sweater isn’t the best look.
2. Keep grooming minimal
Keep things subtle with your grooming routine – wear cologne if that’s your thing, but not too much.
A date is an intimate setting, and you don’t want to overpower her with your scent.
3. Show a little skin
Sure, it’s winter, but do what you can with your outfit to project familiarity and closeness. Try a button-down with the sleeves rolled up, or a sweater that feels soft to your date’s touch.
For casual winter outfits for guys, jeans or chinos are perfectly acceptable. When worn rolled at the cuff, you can flash a little ankle. Heck, if it’s warm out, go for short sleeves!
After all, us ladies like to know what you’re working with, too.
4. Make an (accurate) impression
Of course you want to look your best on a first date, but you should still look like you.
For me, I would never wear sky-high heels on a first date. I don’t want to set expectations that I’m always going to show up looking so fancy. Because let’s be honest, I’m not.
For guys, the same axiom applies.
If you’re a granola-chomping hippie but wear a three-piece suit and wingtips trying to impress your new lady friend, it’ll be hard showing up to date #2 in a hemp hoodie and hiking boots.
When it comes to date night outfits for winter, aim for what you feel best wearing, and also feel your most handsome in.
5. A good place to upgrade? Your footwear
When I do show up in flats for a date, it’s usually not a pair of sneakers.
Even if you’re rocking a date night outfit with jeans, make the effort to step up from your day-to-day sneaks. A pair of lace-up boots or loafers will elevate your look from the everyday.
6. Present the best version of you
You’re going on a date, so please: no holes, tears, rips or (shudder) stains.
Also, skip any clothing that trumpets the designer’s name or logo. Your outfit is like a billboard; it sends a message. You don’t want it to be someone else’s.
Of course, all this advice is for naught if you don’t win over your lady love with your charming personality.
So be curious, kind, and polite!
If you drink, set a limit for your booze intake (even if it helps your nerves!), and – this should go without saying, but I’ll say it anyway – remember to look in her eyes and not at her, well…you know.
Now, go get ‘em.
…I mean, her.
***
feature image: Marina Spichka on Instagram
