Cute Brunch, Bar & Date Night Outfits for Winter

January 12, 2023

Cute Brunch Outfits Winter

It’s cold out there! Having a tough time putting together outfits for brunch, the bar, or a date night in the winter?

This seems to be a common issue for women who like to look good without sacrificing comfort. While it may feel impossible at times to dress for social outings in the winter time, hopefully this post will inspire you to get creative to find cute winter outfits that work for you.

To help you get some ideas for combining fashion and function, here are some favorite winter outfits to try.

Cute Brunch Outfits for Winter

cute brunch outfits winter

Brunch is all about having fun and enjoying the mid-morning (or afternoon) with a great meal and great company.

Whether you’re meeting up with the girls, doing a couples’ brunch, or a birthday brunch, there are plenty of winter brunch outfits you can pull together without sacrificing style or warmth.

Bodycon & Boots

cute brunch outfits winter

A sleek look that can take on many forms depending on your personal style, the bodycon is a fashion classic for a reason.

Easy to layer under a big, fabulous coat and to pair with boots or booties, bodycon dresses are a great piece to build your winter brunch outfit around.

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Styling tip: Try taller (knee-high) boots with midi dresses if you feel like the proportions look off.

Bodysuit & Jeans

cute brunch outfits winter

When getting dressed up for daytime fun, take the chance to wear your favorite fun colors that will pop in the brunch-time sunshine.

Go understated sexy in this casual yet sexy outfit that you can personalize with jewelry, hair style, and shoes.

Bodysuits (or teddies) have so much versatility, and many can be worn without a top layer if desired. Of course, they look amazing underneath your favorite fashionable jacket, too!

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Related: Cool Girl Style—How To Wear Underwear as Outerwear →


Date Night Outfit Ideas for Winter

casual date night outfits winter

Got a hot date on the calendar for a cold night? Worry not about what to wear!

When picking out your date night outfit, think about how much time will be spent inside versus outside and whether or not a heat source will be available. From there, we have some casual and cute options for you to peruse! 


Related: 14 Valentine's Day Date Ideas →


Bodystockings & Jeans

cute brunch outfits winter

If you’re going out for a casual date night this winter, why not get creative with your layers? Wear your favorite pair of sexy denim, but underneath, opt for a sexy bodystocking.

The layering options are endless with bodystockings, and they are an unexpected, hot twist to wearing bodysuits and pantyhose.

Depending on your date activity, you could add a blazer on top, a cute tunic, a cropped sweater or so much more.

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Related: All About Bodystockings →


Dress & Thigh Highs

cute brunch bar date night outfits winter Mixing fashion and function is easy with thigh highs. Plus, they’re ridiculously sexy!

Perfect for date nights where intimacy and romance are on the menu, the dress and thigh high boots combination is always a winner. You could also switch in a skirt and a sweater instead of a dress.

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Shop sexy skirts →

Shop thigh high hosiery → 

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Related: How To Wear Thigh Highs →



Cute Bar Outfit Ideas for Winter

cute bar outfits winter

If you’re going to the bar in winter, you know you’re usually freezing until you get inside. Once you’re inside, it can get very warm. This is tough to dress for!


Mini Dress & Big Coat

bar outfits winter

Our bar outfit solution is to wear what you would normally wear to the bar—a mini dress, maybe—and add a couple weather-appropriate accessories like socks/hosiery and a fabulous, warm coat.

Most bars have coat checks/racks/hangers so you can enjoy yourself unencumbered yet arrive and exit in style.

Shop mini dresses →

Shop socks & hosiery →

Shop plus size socks & hosiery →

Shop heels & boots →

Styling tip: Don’t worry about ruining your hair with a hat—studies have shown you’re more likely to lose heat from exposed arms/legs/hands/feet.


Related: 5 Tips for Winter Outfits Even When It's Freezing →



Are you ready to do brunch, bars, and dates in style this winter?

Although this is not an exhaustive list of winter outfit ideas, hopefully it will get you thinking about some new things you haven’t tried.

Of course a cozy sweater has its time and place, but sometimes you want to flex your fashion chops and dress to impress—even when temperatures are frigid. We support you, Diva!

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