It’s officially 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 winter going-out outfit can you wear 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. It’s a wardrobe struggle worth addressing, once and for all.
“This season, designers showed a range of options on how to stay warm without sacrificing style,” Los Angeles-based stylist Catlin Myers tells TZR. “Sequin jackets, tailored suit coats, and even luxe puffer jackets are all great options.” For starters, it helps to consider all the ways you can wear layers and still look dressed up. That means ensembles centered around a jumpsuit, sweater, 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. “Try mixing and matching — a party dress with a leather puffer or suit coat — or incorporating a metallic tall boot or printed jacket to dress up something more casual,” says Myers. Statement outerwear is key. 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 night out on the town, a first date, or a humble house party, here are 24 easy ideas for how to dress to thrill while still dressing for the chill.
We only include products that have been independently selected by TZR's editorial team. However, we may receive a portion of sales if you purchase a product through a link in this article.
Outerwear Meets Slip
Simple but effective. Oversized sweaters and long midi dresses are always a yes — especially when it gets chilly outside. Dress up slouchy vibes with a silky slip dress (or skirt) and a strappy heel for a cozy but stylish winter night-out look.
Dressed Up Jeans
What is a winter going out outfit without a longline wool coat? Since a trendy winter coat is such a staple, you can really keep the rest of your look simple with a pair of jeans and an extra chunky sweater. Pair with thick hoops, a chic crossbody, and cleated boots, and you’re ready to hit the town.
It’s easy to think that winter night out outfits have to be extra festive when the holidays are so closely associated with the season — but try your hand veering in the opposite direction. Limit your shade range to browns and tans with a wool jacket or quarter zip with black pants and boots for a muted, understated look.
Winter is all about the warm, chocolatey tones seen in this comfy puffer. Incorporate a bit of variety in your winter outfit’s silhouettes by matching an oversized down jacket with wide, relaxed pants. Then, by playing up the shapes of your pieces, this allows you to keep textures and colors on the DL.
Cold Weather Academia
Who says you can’t channel your inner Gossip Girl in sub-zero temps? Pull from the ranks of school uniform chic’s best and warm it up with crisp, tailored blazer and leather boots. Add wide-leg trousers or a matching skirt with tights underneath.
Great winter night out outfits are all in a good selection of winter whites. Pearlescent tones are reminiscent of snowflakes, which makes this look all the more suited to the season. Balance a simple white dress with a fun statement bag, in white or another shade for a pop of color.
All That Sparkles
All that glitters is the name of the game. Amp up a winter night outfit with a sweater-skirt combo and a lot 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.
Heat up your night-out outfit with a fiery color palette. A scarlet blazer and matching pants in shiny red patent are certain to smolder, no matter what the evening brings.
The best winter night out outfits are not shy on the glimmer. A shiny copper midi skirt and designer logo tee or sweatshirt make 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.
Breathe fresh air into a cold-weather look with a winter-friendly spin on feminine pastels. It’s all about layers and textures. A matching knit set is chic as is, but a pastel puffer is what really takes an outfit like this to the next level. If you can't find a puffer in your desired shade, you can achieve a similar look by layering with a separate cable-knit sweater.
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.
Hungry for something with trend power to spare? Step out in a tapestry blazer dress with tailored pants for an elevated, too-cool-to-be-bothered vibe. If you’re up for baring some skin in the cold, a crop top adds a sultry touch to this outfit.
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 pants you can find, and a pair of chunky boots. You’ll have zero regrets when it’s 2 a.m. and 32-degrees and you’re still feeling comfy.
Metallics were made for this time of year. A gold lamé blouse, pants, or skirt is just the disco-inspired touch you need to liven up your winter wardrobe before you hit the club. Wear it with neutrals for a cool rock-and-roll vibe and prepare to relive the heyday of nightlife that was the ‘70s and ‘80s.
If you’re the type who wants to look edgy and unique when you go out, try this year’s hottest celeb trend: catsuits. This full-body piece makes the perfect one-and-done look — unless, of course, you want to accessorize.
There’s nothing like a pair of brightly-colored pants to get you through your winter social calendar in style. This neon colorblock look makes for an eye-catching ensemble that’s pretty much impossible for your friends to miss in a crowd.
Slouchy knitwear may not be the first thing you reach for when dressing for an evening out, but make it matching, body-skimming silhouette and you’d be surprised just how sultry a full sweater ensemble can look.
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 printed slip dress under a pastel blazer. The result is maximum glamour.
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 python flares with a cropped sweater, heels, and a crossbody bag.
Luxe brocade or metallic jacquard is ideal for winter evening wear, especially when done up in tailored separates. Cinch the shape with a belt to define your waist and elongate the leg line, and keep the rest of the look sleek and streamlined.
Embrace the intergalactic aesthetic with a metallic two-piece paired with colorful makeup and a flirty Y2K hairstyle. Not only will you stay warm all night, but you’ll also be wearing one of the most unique looks at the party. All eyes on me, please!
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 offers 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 (like a turtleneck) up top.
Laid-Back Meets Sporty
Hoping to get away with wearing sweatpants to dinner? Layer your favorite loungewear with a tailored blazer, chunky sneakers, and a baseball cap. You’ll look casual with just the right hint of fashion girl chic.
This article was originally published on