We’re inching closer and closer to 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 stand out in a crowd without leaving you frozen and bitterly uncomfortable? The looking chic versus feeling comfortable quandary is never more relevant than leading up to and during the holiday party circuit — and it’s a wardrobe struggle worth addressing, once and for all.
“Designers are showing 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 will take your overall look up a notch, not an obligatory, outfit-ruining coat you can’t wait to take off the second you’re instead.
Whether it’s a night out on the town, a first date, or a humble house party, here are 22 easy ideas on dressing to thrill ... and for the chill.
Sweater + Slinky Slip Dress
Oversized sweaters and long midi dresses are always a yes, especially when it gets chilly outside. Dress up slouchy silhouettes with a silky slip dress (or skirt) and a strappy heel for a cozy but stylish winter night-out look.
Jeans + Elegant Coat
What is a winter evening outfit without a longline wool coat? By deploying a sophisticated neutral design on top, you can really keep the rest of your look simple with a pair of jeans and an extra chunky sweater.
Neutral Tones
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 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 chic, understated look.
Relaxed Fits
Winter is all about the warm, chocolatey tones seen in this comfy puffer. Incorporate a bit of variety by matching an oversized down jacket with wide, relaxed pants. By playing up the shapes of your pieces, you can keep keep textures and colors on the DL.
Winter Whites
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 burst 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.
Red Hot
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.
Casual Shine
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.
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 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.
Luxe Velvet
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 skinny heel booties.
Structured Shimmer
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.
Cozy Knits
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 by throwing 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.
Disco Lamé
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 look before hitting 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.
Catsuit Glam
If you’re the type who wants to look edgy and unique when you go out, try a sultry catsuit. This full-body piece makes the perfect one-and-done look — unless, of course, you want to accessorize.
Party Pants
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.
Wild Side
Animal prints are having a major moment this season, and are just begging for a place among your go-to party attire. Translate the trend to a chilly night out by layering a printed slip dress under a pastel blazer. The result is full-on glamour.
Snake Print Pants
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 pants with a cropped sweater, heels, and a crossbody bag.
Sparkly Separates
Luxe brocade, metallic jacquard, or full-on sequins are 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 streamlined.
‘80s Redux
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!
Satin 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 offers some much-needed weight and coverage to offset the featherweight fabric. 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.
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