17 Cute Outfits for Winter that Will Have You Feeling Stylish (and Warm)
While most of your fall pieces can easily be transitioned into cute outfits for winter, you may need to add a few additional staples we are loving this season.
While we understand the feminine urge to grab your favorite graphic sweatshirt and throw it atop your forgiving Lululemon Align leggings, sometimes exploring your personal style and trying something new is just more fun. Who knows? Maybe you’ll find you have a knack for layering or you love the way you look in cropped sweaters and straight leg jeans.
1. Puffer Jacket and Sweats
Puffer jackets are a necessity during winter but can easily look like a drab sleeping bag. Try one in a lighter hue and layer it atop a matching sweat set. By keeping the sweats fitted and accessorizing with a cute pair of sneakers and a crossbody bag, you’ll look stylish and comfy.
2. Faux Leather Pants and a Sweater
Switch up your basic denim and try a warm pair of faux leather pants. This sleek staple will elevate a simple OOTD and add a dash of grunge. Add a turtleneck sweater and some coordinating flats or booties to complete your chic ensemble.
Shop similar styles: Abercrombie & Fitch Vegan Leather 90s Straight Pants ($99); Madewell Ruffle Neck Sweater ($88; $60)
3. Tights with Dress or Skirt
While adding a pair of sheer or opaque tights under your skirt or dress will give your legs a bit more coverage on a cold winter night, that’s not the only reason we love them. The simple addition also adds a sultry, yet classy element without taking away from the rest of your outfit.
4. Cropped Sweater and High-Waisted Straight Jeans
A high-waisted pant paired with a cropped sweater will elongate your legs and show off your shape. We love how the thicker sweater material contrasts with the denim and adds dimension and texture to an otherwise basic look.
5. Longline Coat and Baseball Cap
A polished, long coat with clean lines will balance out the athletic vibes of a baseball cap (which is a chic way to cover greasy roots). This popular pairing is a trusty go-to if you can’t decide what to wear while running errands or hanging out with friends.
6. Sweatshirt Under Oversized Blazer
Like the baseball cap and longline coat, this look combines sophistication and sportiness, which are a match made in heaven. Whether you choose a leather blazer or wool, make sure it’s a bit oversized to accommodate the sweatshirt underneath.
7. Longline Sherpa Coat, Jeans and White Sneakers
When in doubt, throwing on this cozy coat will make anything underneath look more stylish. Since this coat has many elements to it—the Sherpa material, long length and oversized fit—it’s best paired with basic jeans and white sneakers so it can be the star of the show.
8. Chelsea Boots and Leather Leggings
Another way to wear leather leggings? With a pair of Chelsea boots. The contrast of a skin-tight legging with a chunky boot creates an on-trend grungy style that’s perfect for walking through the streets of NYC—or anywhere else.
9. Button-Front Cardigan, Flare Leg Pants and Pointed Booties
This cute option is a fun alternative to your regular pullover sweater. We like the idea of keeping a button or two open for a flirtier look and would pair the cardi with flared pants and pointed booties.
10. Turtleneck under Sweater Vest
The academia trend is still going strong and if that means we get to wear more sweater vests and turtlenecks, we’re here for it. Layer over a skirt or your favorite pair of pants to round out that prep school look for winter.
Shop similar looks: Abercrombie and Fitch Slim Turtleneck Sweater Bodysuit ($69; $59), Abercrombie and Fitch Cropped Fuzzy V-Neck Sweater Vest ($55; $33)
11. Hair Bows and Dresses
A hair accessory can change the vibe of any outfit. Our favorite, though, is a hair bow with a dress. Whether you’re headed out for the night with friends or to a holiday party, your ensemble will be made all the more glamorous by throwing a bow in your hair. With the rising popularity of hair bows, you have your pick of designs for whatever dress you’re accessorizing. Plus, they’re relatively inexpensive and usually come in a multi-pack.
12. Sleek Turtlenecks under Chunky Knits
Layering pieces that can be worn individually is a great way to add some dimension to your outfit. Case in point: A thinner piece, like a turtleneck shirt, will complement the texture and thickness of a knit sweater.
13. Sweater Vest Dresses with Knee-High Boots
Similar to the sweater vest above, the dress version is equally sophisticated and cute. Throw a collared button down underneath and complete the look with some high boots to contrast the shortness of the dress (and keep your legs warm).
14. Leather Blazer and Leather Pants
If a grungy aesthetic suits you, you’re going to love this all-leather style. Wear a simple T-shirt underneath to keep the look streamlined.
Shop similar styles: Abercrombie & Fitch Vegan Leather 90s Straight Pants ($99), BLANKNYC Vegan Leather Blazer ($128)
15. Sweater over Slip Dress
This relaxed ensemble is reminiscent of one of our favorite 2020 fashion trends: Cottagecore (but the winter version). Grab an oversized cardigan to wear over a satin midi dress for the cold weather coverage needed this season.
16. Puffer Vest, Chunky Boots and Mini Dress
This is another instance where chunky and oversized outerwear and shoes work, as long as they’re paired with a more understated piece underneath like a simple mini dress.
17. Bold Pants and Matching Jacket
Whether your sartorial inspiration comes from Aimee Song or Kamala Harris, these matching power suits scream high fashion. Try the look in a bold color like cobalt or emerald—or in a velvet material for the holiday season.