17 Cute Outfits for Winter that Will Have You Feeling Stylish (and Warm)

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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.

From a leather blazer with a turtleneck to some sheer black tights and a mini dress these 17 outfit combos have us excited to strut our street style.

puffer jacket w sweats
Getty Images/Edward Berthelot

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.

Shop similar styles: Champion Classic Reverse Weave Sweatpant ($50), Champion Classic Reverse Weave Sweatshirt ($54), ASOS Longline Puffer Jacket ($171)

leather pants and sweaters
Getty Images/BG020/Bauer-Griffin

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)

tights with skirt
Getty Images/Edward Berthelot

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.

Shop similar styles: Lechery Pellis 5 Ultra Sheer Tights ($48), BP. Long Sleeve Velour Mini Dress ($46)

jeans and cropped sweater
Getty Images/John Sciulli

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.

Shop similar styles: Madewell The Perfect Vintage Straight Jean ($128), Michael Costello x Revolve Peek A Boo Crop Top ($188)

hats and long coat
Getty Images/Edward Berthelot

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.

Shop similar styles: New Look Belted Tailored Coat ($93), MLB Baseball Hat ($32)

blazer sweatshirt
Getty Images/Edward Berthelot

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.

Shop similar styles: Everlane The Oversized Blazer ($185), Pull&Bear Oversized Hoodie ($30)

teddy coat and sneakers
Getty Images/Streetstyleshooters

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.

Shop similar styles: Abercrombie & Fitch Oversized Sherpa Teddy Coat ($180); On Roger Clubhouse Sneaker ($150), Madewell High-Rise Slim Straight Jeans ($88)

leather pants and chelsea boots
Getty Images/Edward Berthelot

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.

Shop similar styles: Caslon Miller Waterproof Chelsea Boot ($100), Spanx Faux Leather Leggings ($98)

button up cardigan
Getty Images/Bellocqimages/Bauer-Griffin

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.

Shop similar looks: UO Peyton Fitted Cropped Cardigan ($49); Levi’s ‘70s High Rise Flare ($90), Steve Madden Thrived Bootie ($130)

sweater vest and turtleneck
Getty Images/Melodie Jeng

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)

hair bows and dresses
Getty Images/Roy Rochlin

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.

Shop similar options: Madewell Two-Pack Velvet Bow Hair Elastic ($19); Charles Henry Smocked Long Sleeve Mini Dress ($89)

turtleneck and chunky knit

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.

Shop similar styles: H&M Rib-Knit Cardigan ($35; $30), Everlane The Organic Cotton Tissue Turtleneck ($40)

sweater vest dress

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).

Shop similar styles: Abercrombie and Fitch Sweater Vest Mini Dress ($79; $67), Chinese Laundry Crafty Knee-High Boot ($160)

all leather
Getty Images/Jeremy Moeller

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)

slip dress and sweater
Jenni Kayne

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.

Shop similar styles: Jenni Kayne Cashmere Cocoon Cardigan ($445), ASOS Cami Midi Slip Dress ($64)

puffer vests
Getty Images/Jeremy Moeller

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.

Shop similar styles: Vince Camuto Melleya Over the Knee Boots ($170; $127), ASOS Puffer Vest ($54), BP. Fitted Slit Long Sleeve Rib Dress ($39)

pant suit
Getty Images/Melodie Jeng

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.

Shop similar styles: ASOS Velvet Suit Blazer ($43), ASOS Velvet Suit Flare Pants ($32)

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Commerce Editor

Olivia Dubyak is PureWow's Commerce Editor and textbook Capricorn. She studied journalism at Duquesne University in Pittsburgh, Pennsylvania, but has gone from New York City to...