Shopping·7 min read

Stylish Winter Wardrobe Staples That'll Actually Keep You Warm

Cute Winter Outfits That Will Actually Keep You Warm
Design: theSkimm | Image: Free People, Girlfriend Collective
December 20, 2022

Products you buy through our links may earn us a commission. Oh, and if something's out of stock, oops, it was there (and all prices were accurate) at time of publication.

From cropped vests perfect for the beginning of the season to accessories that’ll keep you layered like a pro, here are some of our fave pieces for winter outfits that’ll actually keep you warm without sacrificing on style. And if you’ve got a winter wedding on the agenda, fitness goals to achieve, or a budget to keep, we’ve got cold-weather solutions for that too. Let’s get cozy.

Cute winter outfits
Free People

A cropped winter vest that’ll go with everything…

And we mean everything. Layer it on top of your fave workout outfit or throw it on over a fitted dress for some extra warmth on a night out. It’s got a zip-front closure, an exaggerated collar that can be zipped up to create a turtleneck fit, and defined shoulders to make pairing it with even the flowiest of dresses look chic. Yes, please. ($128, Free People)

Buy it
Cute winter outfits
Amazon

A sweater dress you can style up or down…

It’s made from a cotton and polyester blend and can be machine-washed. Wear it with tights or leggings and some warm boots during the colder months, and pair it with your favorite belt to create a stylish silhouette. Comfy, cute, and versatile? Check, check, aaaand check. ($16.70+, Amazon)

Buy it
cute winter outfits
Girlfriend Collective

A super-cozy fleece jacket you’ll never want to take off…

This half-zip is made from 100% recycled plastic bottles and has double-sided fleece for softness on the inside and outside. It’s got zippered pockets and it’s available in tons of colorways and sizes XXS–6XL. Hi, new layering go-to. ($128, Girlfriend Collective)

Buy it
cute winter outfits
Free People

A long-sleeved maxi dress for an effortless look…

We’re talking throw it on and head out the door in minutes. The top features a henley-style button neckline and the dress has a roomy, relaxed fit that makes it a great design for layering. Snag it in one of six colors and pair it with warm accessories like a comfy hat and cute booties now — then wear it on its own with your fave sneakers or sandals come springtime. ($98, Free People)

Buy it
cute winter outfits
Camper

Comfy knee-high boots with a trendy silhouette…

We love the futuristic design that’ll stay on trend season after season and the knee-high fit that’ll keep your calves toasty. The pair is made with Tencel Lyocell uppers, Ortholite footbeds, and PU outsoles so you know they’ll be some of the comfiest boots you’ve ever worn. And with a 2.5-inch heel, they’ll give you just the right amount of lift too. ($180, Camper)

Buy it
cute winter outfits
Nordstrom

Puffy winter boots perfect for snowy walks…

Slush, sleet, rain, puddles — they’ve got nothing on these bad boys. If you’re looking for some boots that’ll deliver serious functionality throughout the winter months, look no further. This pair is waterproof and made with a recycled-fleece lining to keep you warm and dry. We love the thick rubber sole that’ll keep you from slipping and sliding (sans blisters) at the end of the day. Snag ’em in one of four colorways — including our fave, cream and pink — and enjoy your winter adventures comfortably. ($175, Nordstrom)

Buy it
cute winter outfits
Quince

A cashmere turtleneck you won’t wanna take off…

We have a feeling this classic design will become your new winter wardrobe staple. The Mongolian cashmere sweater from this HQ’r fave brand comes in seven different colors and is made with sustainably sourced materials that are three times as warm as wool. Customers say it fits true to size and keeps them nice and toasty. Pair it with a slim maxi skirt or a pair of formfitting jeans to look effortlessly pulled together. Don’t mind if we do. ($79.90, Quince)

Buy it
cute winter outfits
J. Crew

A sweater-blazer that’ll only add to a professional look…

If you want to keep things cozy without dressing down, this sweater-blazer is your answer. Pair it with the turtleneck above for an office-ready look or throw it on top of your athleisure for your next grocery run. It’s made from a lightweight cotton blend, so you can easily layer it under your coat or jacket during your commute when cold outside. It’s also got two front patch pockets to slip your hands into. ($59.50+, J.Crew)

Buy it
cute winter outfits
Free People

An oversized balaclava that’ll keep your head and neck covered…

For anyone who isn’t a hat person, we present this cozy option. Use it in place of a scarf (or if it’s seriously cold, double up for extra warmth), under your coat’s hood, or over earmuffs. It’s made with a ribbed knit and has a drawstring close. Freezing ears, begone. ($48, Free People)

Buy it
cute winter outfits
Amazon

Fluffy earmuffs you can take with you everywhere…

Since they can fold, bend, and twist to fit into your purse or backpack. They’re super-soft and have an exaggerated eye-catching look, and customers say they cover their whole ears. These come in six different colors and have a one-size-fits-all design that’ll make sharing or gifting a cinch. ($16.88+, Amazon)

Buy it
cute winter outfits
Torrid

A glitter jumpsuit with long sleeves…

Otherwise known as a great party option for when it’s beyond chilly outside. The sweetheart neckline is sure to flatter. And if you stress out over putting together an outfit, a jumpsuit knocks out half the frustration. All you’ve gotta do now is pick out your shoes and earrings. ($47.75, Torrid)

Buy it

Live Smarter

Sign up for the Daily Skimm email newsletter. Delivered to your inbox every morning and prepares you for your day in minutes.