Winter Date Night Outfits for Guys | Men's Style Ideas

Winter Date Night Outfits for Guys

Winter Date Night Outfits for Guys
Cold weather romance
elf movie

By Jennifer Hunter | Last Updated: Nov 6 2022 | 9 min read

There’s enough to worry about when headed into a winter date—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 winter date night outfits for guys.

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? A neighborhood 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 stylish winter date outfits 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:

Below, 8 men’s winter date night outfits:

winter date outfits for guys

Winter Date Night Outfit #1

men's winter date outfit

The look: Corduroy pants, a cozy button-down, and loafers

SG Says: You’ll be sure to impress in a pair of textured pants coupled with—drumroll please—even more texture up top!

If it’s warm-ish out, skip the socks and cuff the pants to flash some ankle.

Shop the outfit:

Winter Date Night Outfit #2

men's winter date outfit

The look: Cream city with a bomber on top

SG Says: If you’re worried about stains with this mostly off-white outfit, might we suggest skipping the ketchup if you order fries?

Shop the outfit:

Winter Date Night Outfit #3

casual men's winter date outfit

The look: navy monochrome with a pop of plaid

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.

Shop the outfit:

Winter Date Night Outfit #4

men's winter date outfit with jeans

The look: Casual cool

SG Says: This look screams “Let’s meet up later for drinks downtown.”

Totally cool and casual in the best way possible.

Shop the outfit:

Winter Date Night Outfit #5

stylish winter date outfit for men

The look: Dressy casual

SG Says: If you want to dress up without looking and feeling stuffy, this is the perfect outfit.

Performance trousers with a polo sweater in a winter-y neutral and statement sneakers.

Shop the outfit:

Winter Date Night Outfit #6

casual winter date outfit for guys

The look: city-dwelling lumberjack man

SG Says: Our whole team loves this plaid shirt from Corridor. It gives the wearer an elevated vibe without working too hard at it.

Shop the outfit:

Winter Date Night Outfit #7

men's winter date outfit

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 look would be perfect for a winter date night outfit.

Sorry not sorry! The youths will take over the earth, might as well cede some (style) ground now.

Shop the outfit:

Winter Date Night Outfit #8

men's winter date outfit with turtleneck

The look: Casual sophistication

SG Says: A list of can’t-miss winter date night outfits would be incomplete without at least one turtleneck.

This look is anything but stuffy, with sneakers and light-wash jeans to keep the overall effect laid-back.

Shop the outfit:

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Before you go!

Check out a few #SGapproved pre-date tips below…

1. Change before the date

elf movie 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.

Jeans or chinos are perfectly acceptable, and 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

buddy the elf

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.

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

all images: Elf, 2003 (New Line Cinema)

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. 


Want more style support for winter date night outfits? Team SG can create a customized shopping plan with outfit ideas just for you!