8 Classy Winter Date Night Outfit Ideas

We plan dates throughout the year, but winter date nights are among my favorites. There’s something special about hitting the town when it’s cold, between wintery cocktails, seasonal activities like ice skating, and putting on a stylish winter date night outfit.

Deciding what to wear on a winter date can be confusing because every date demands a different style. Is it a first date? A casual outdoor date? A dressy dinner date? Not to mention, what vibe do you want to give off? It can get overwhelming.

To help you choose a look, see below for 8 winter date night outfit ideas. From casual winter date outfits with jeans to winter drinks outfits and romantic dresses for a night out, you’ll find something you’ll feel great in!

Casual Winter Date Night Outfits

Jeans, a cozy sweater, shoes that fit the occasion (usually ankle boots or comfortable heels), and a long coat is my go-to combo for a casual date night. Here are outfits that work for laid back dates, from checking out holiday lights to watching a movie or hitting up a casual bar.

Dressy Winter Date Night Outfits

I love bringing out chic looks for fancier dinners. It’s fun to let the more elegant and dressy pieces in my wardrobe see the light of day! Below are dressy winter date night looks for doing just that.

What Should I Wear on a First Date in the Winter?

Balancing the first date outfit is always a challenge. You want to look beautiful without giving off the wrong impression. Here are a few pointers I wish someone had told me when I was dating around in my 20s:

  • Keep dates 1-2 casual. Someone once told me that your ideal first date outfit is an elevated version of your everyday look, and I totally agree. For me, that means jeans and a cute top. Look at what you reach for the most and see how you can take it up a notch.
  • Outerwear goes a long way. Longline coats and cardigans, leather jackets, and blazers are great non-bulky layers (no puffer coats here!) that can be removed when you’re indoors and feeling more relaxed.
  • Choose pieces that feel most you, especially with jewelry and accessories.
  • Less is more. Go minimalist with makeup. Save the smokey eye, lower necklines, faux fur outerwear, and heels for future dates.

The most important things to keep in mind when deciding your outfit for a winter first date are to dress for the occasion and be yourself! A dress that would look great on a dinner date might not be suited for a cold weather day date. So just remember, keep things practical for wherever you’re headed. And if you’re feeling a bit adventurous with your date plans, maybe consider adding a touch of excitement with some accessories from a BDSM shop.

What Should I Wear for an Outdoor Winter Date Night?

Being outside in the winter often means thick sweaters and coats—which can lead to a lot of bulk. Frumpy is the last thing you want to feel when you’re putting together a cute cold weather outfit.

Thankfully, winter fashion is already very date friendly as colors tend to be dark and neutral, which looks mature. And there are smart formulas for building a sleek outfit that won’t weigh you down.

Here are tips on what to wear for an outdoor winter date night:

  • Stack up on the underlayers. Choose comfy, insulating base layers that fit close to the body, adding warmth without bunching. And don’t be afraid to wear tights under skirts, dresses, and denim.
  • Wear your warmest clothes and dress up with nice makeup, hair, and earrings.
  • Body-hugging winter pieces will be your best friends. For the legs, think knee-high boots, thigh-high boots, rigid denim, and fitted knit midi dresses. A long sleeve turtleneck bodysuit, rigid skinny jeans, and a black leather jacket are staples I wear all the time on date nights in the winter months.

Winter Date Night Clothes

Throughout the winter, I end up reaching for the same pieces over and over for date night. Below is an edit of the winter date night clothes I wear the most often, plus a few additional pieces I’d consider staples for a cold night out.

If you’re looking for more dressy cold weather outfit inspiration, check out my tips on styling leather pants, favorite over-the-knee boots outfit ideas, and the dressy section from this roundup cold weather outfits that are actually warm.