19 Going-Out Outfits That Won't Leave You Cold And Full Of Regret This Winter


We’ve officially passed the winter solstice and entered the season of below freezing temps. Dressing for frigid days means bundling up in endless knits and woolen layers, but the evening presents an entirely separate challenge. What going-out outfit can you wear on a winter night that'll look fashionable without leaving you frozen and bitterly uncomfortable? The looking chic versus feeling comfortable quandary is never more relevant than during the holiday party circuit and New Year’s Eve celebrations, but it continues to come up well into February and March too, so it’s a wardrobe struggle worth addressing, once and for all.

For starters, it helps to consider all the ways you can wear pants and still look dressed up. That means ensembles centered around a jumpsuit, tailored suiting, or leather leggings should be top of mind. When you do opt to wear strappy dresses or miniskirts that expose your legs, long sleeves, extra layers, and black tights will be your new best friends since you'll need a little extra coverage. Statement outerwear is key, too. Choose a topper that can integrate as a stylish element of your overall look, not just the obligatory, outfit-ruining coat you can’t wait to take off once you step inside. Whether it’s a girls' night out on the town, a first date, or a humble house party, here are 19 easy ideas for how to dress to thrill while still dressing for the chill.

Winter Whites

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Winter whites are always a yes, and pearlescent paillettes and lace appliqués read like snowflakes, which makes this look all the more suited to the season. Balance the whimsical quality of an icy cut-out skirt with a crisp menswear button-down and classic black boots.

All That Sparkles


All that glitters is the name of the game. Amp up a sweater-skirt combo with a healthy dose of glitz. If the sequined fabric isn’t enough, add extra sparkle with rhinestone-embellished accessories, dangly crystal earrings, and sparkly hosiery.

Lots of Leather


Leather lovers, rejoice! Your season is here. Embrace biker babe vibes in an ‘80s-inspired leather mini dress and thigh-high boots. Polish the look with polka-dot stockings for a feminine touch and top it off with a knit beanie for extra resistance against the frosty air.

Red Hot

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Heat up your night-out outfit with a fiery color palette. A scarlet blazer and matching pants in shiny red patent is certain to smolder, no matter what the evening brings.

Casual Shine


A shiny copper midi skirt and designer logo tee or sweatshirt makes for a stylish balance of dressy and casual. Make it work for winter by adding your favorite leather moto jacket and a pair of sock-boots.

Wintertime Pastels


Breathe fresh air into a cold-weather look with a winter-friendly spin on feminine pastels. It’s all about layers and textures. A long sweater dress and candy-colored satin trousers are chic as is, but the pastel puffer is what really takes an outfit like this to the next level. If you can't find a puffer with a fuzzy lining like the one above, you can achieve a similar look by layering with a separate faux fur jacket.

Velvet MVP

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When in doubt, add a velvet blazer in a rich jewel tone. This wintertime MVP will transform practically anything into a luxe evening ensemble, but it looks especially perfect with a sleek black skirt and heeled booties.

Midnight Cowboy

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Hungry for something with trend power to spare? Step out in a tapestry blazer dress and western boots with an oversized shearling coat to keep things cozy. If the thought of bare legs has you scared, just add black tights in whatever denier the temperatures demand.



Sometimes it’s hard to bring yourself to put on anything other than your biggest, slouchiest sweater while winter’s bitter chill rages on outside. If you’re a knitwear-24/7 type, lean into your predilection without an ounce of shame. Throw on an oversized jumper (a big sweatshirt works too), the thickest black tights you can find, and a pair of party heels. You’ll have zero regrets when it’s 2 a.m. and 32-degrees and you’re still comfy AF.

Disco Fever

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Metallics were made for this time of year. A gold lamé blouse is just the disco-inspired touch you need to liven up your winter wardrobe before you hit the club. Wear it with leather pants for a cool rock-and-roll vibe and prepare to relive the heyday of nightlife that was the ‘70s and ‘80s.

Rocker Chic

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City girls are known for their love of a high-low mix. If you’re the type who wants to look edgy and unique when you go out, but not like you tried too hard, consider pairing a cropped vintage sweatshirt with velvet flares for a look that’s equal parts cool and casual. (Not to mention very high on the comfort scale.)

Party Pants


There’s nothing like a pair of party pants to get you through your winter social calendar in style. Black trousers feel festive and fun with a high waist and shiny embellishments. Wear them with puff-sleeved blouse to up the fancy ante.

Sweater Weather

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Slouchy knitwear may not be the first thing you reach for when dressing for an evening out, but make it an off-the-shoulder silhouette and bring in a thigh-high slit or two and you’d be surprised just how sultry a full sweater ensemble can look.

Wild Side


Animal print is having a major moment this season, and it’s just begging for a place among your go-to party attire. Incorporate the trend for a chilly night out by layering a fitted long-sleeve leopard top under a lingerie-inspired slip dress. The result is maximum glamour.

Snake Chic

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If you’re looking to tap into the animal prints trend without skewing so dressy and done-up, snakeskin trousers are the cool-girl alternative approach to the exotic motif. Pair black-and-white python pants with a form-fitting bodysuit and finish the ‘90s-inspired ‘fit with a fur-trimmed coat, a very on-trend clear PVC bag, and minimalist black shoes. Oh, and don't forget to swipe on a deep plummy-brown lip color before you head out the door.

Suit Yourself

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Luxe brocade or metallic jacquard is ideal for winter evening wear, especially when done up in tailored suit separates. Cinch the shape with a wide belt to define your waist and elongate the leg line, and keep the rest of the look sleek and streamlined.

'80s Redux

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You don’t need to retire your shoulder-baring styles at the first sign of winter weather. Extend the life of a strapless jumpsuit by layering it over a basic black top and adding chunky ankle boots. If you want to embrace the '80s aesthetic, choose a metallic version like the one above and look for a top with strong, structured shoulders.

Slick Slip


The silk slip dress is a staple in the summer, but it can work for cooler weather as well with the help of a little layering. A patent trench coat and tall suede boots offer some much-needed weight and coverage to offset the flimsy frock. If that’s still not enough, add tights on the bottom and a fitted base layer up top.

Sexy Meets Sporty

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The see-through look isn't for the faint of heart. However, if you’re looking to test the waters, it (surprisingly) might be easier to try for the first time in winter. Unlike spring and summer when going sheer means dealing with undergarments and revealing a daring amount of skin, in winter you can get away with layering over base layers and other pieces. For a beginner-friendly look, wear a beaded naked dress over black leggings or tights and a sporty turtleneck.