21 Sweater Outfits So You Stay Cute, Warm and Cozy This Chilly Season

As a fashion gal, I admit that fall and winter are probably my favorite seasons for style. Colder temperatures allow you the ability to layer your outfits, and one of the most important elements of layering is having a good sweater! You can style a sweater with literally anything in your closet: with jeans for a casual look, trousers for work, a skirt for a night out with your friends, or even with sweats for chillin’ at home!

Now, you may already have a handful of sweaters in your closet, or maybe you’re looking to invest in some new ones for the winter. Regardless, I want to help you figure out how to look effortless while wearing them! Below, I’ve compiled 21 stellar street-style sweater outfits. They range in style: some formal, some casual, some sweater dresses, and some sweater vests! Use this as outfit inspo for your next sweater outfit, or treat yourself to some new pieces for the chilly season! Happy shopping, friends 🙂

A Simple Cardigan

A simple cardigan will work wonders for you in the cold weather. Wear it buttoned up with a pair of low-rise baggy jeans and a sleek pointed-toe kitten heel.

Aritzia Cashmere Relaxed Crew Cardigan

Garage Low Rise Baggy Jeans

Marc Fisher Iggy Dress Bootie

A Cropped Look

PSA: you don’t need to buy a cropped sweater for a crop top moment. Simply tuck your sweater into your bra to achieve the look! I promise you’ll get so much more use out of a full-length sweater over a cropped one.

Australian Merino Wool Cable Sweater

Now 82% Off

Pacsun Seaweed Cargo Dad Pants

Now 52% Off

Circus NY Tara Slingback Heel

With a Mini Skirt

This fall and winter, pair an oversized cardigan with a cute mini skirt and a pair of Mary Jane flats. Don’t forget a pair of tights if your legs get cold!

LILLUSORY Women Oversized Cardigan Sweater

Antonio Melani Rosy Houndstooth High Rise A-Line Mini Coordinating Skirt

Sam Edelman Michaela Mary Jane Flat

Incorporate a Print or Graphic

It’s always fun to add prints or patterns to your style. Try pairing a graphic sweater with a neutral-colored skirt and a cute bag that brings out a color from the sweater.

Ralph Lauren Intarsia Knit Dachshund Sweater

Los Angeles Apparel Tennis Skirt

Small Stella Texas Braided Dark Brown

With Wide Leg Jeans

Style a bright yellow sweater with a pair of comfortable wide-leg jeans and a black boot. It’s a simple outfit, but it gets the job done!

Good American Good Ease Relaxed Jeans

AMY LYNN Chelsea Yellow Leather Tote Bag

A Sweater Vest

A sweater vest is a great layering piece. You can opt for a long sleeve, short sleeve, or tank underneath it. Or, on a warmer day, style a sweater vest with no undershirt. For a cool-girl look, pair your sweater vest with a long denim skirt and some cute ballet flats.

Ganni Multicolor Stripe Vest

BLANKNYC Denim Skirt in Black

A Professional Pick

If you’re looking to wear your sweater in a more professional setting, try pairing a simple black crew neck with trousers and a long coat.

Gap 365 High Rise Brushed Twill Trousers

Everlane The Boxy Sweater in Everyday Cotton

AllSaints Mabel Double Breasted Coat

A Floral Cardigan

Keep your outfit fun and colorful by styling a floral cardigan and some matching pants!

Madewell The Emmett Wide-Leg Pant in Corduroy: Welt Pocket Edition

BLANKNYC Flower Cardigan in Sweet Soul

Hana Medium Faux Suede Tote Bag – Brown

With Metallic Pants

Metallic pants were one of the biggest fashion trends a few seasons ago. If you have a pair or are interested in styling some yourself, try wearing them with a white sweater and white accessories. This ‘fit would be sooo perfect for the upcoming holiday season!

Levi’s 501 90s Ankle Jeans

A Sweater Dress

For an easy outfit, style a long sweater dress with a simple black bag and some sunnies. Opt for a closed-toed heel or boot if the weather is chilly!

Brandon Blackwood Luna Zip Leather Shoulder Bag

Reformation Livia Regenerative Merino Sweater Dress

Elisa Johnson Cookie 54mm Cat Eye Sunglasses

A V-Neck Sweater

I’m all for a preppy moment! To achieve this look, style a v-neck sweater with a pleated mini skirt.

Lacoste Women’s V-Neck Cable Knit Cotton Tennis Sweater

Now 50% Off

TONCHENGSD Women’s High Waist Pleated Mini Skirt Skater Tennis Skirt

Vans Old Skool Pig Suede Shoe

Now 31% Off

A Monochrome Look

I love a monochrome outfit like this one. Try styling a black sweater with faded black jeans, a black bag, and some kitten heels.

NA-KD Turtle Neck Knitted Sweater

We The Free Tinsley Baggy High-Rise Jeans

Schutz Women’s Ruth Embellished Slingback Pumps

With a Maxi Skirt

Stay cozy and look cute in the cold weather by styling a striped sweater with a maxi skirt. Finish the look with a comfortable pair of Chucks!

Hill House Home The Delphine Nap Skirt

Z Supply Black Josephine Stripe Turtleneck

With a Bold Accessory

A bold accessory can make any outfit more interesting. Next time you think your outfit is looking a little plain, try adding a bold scarf for some color!

Free People Stripe Hair Scarf

Mango Round-neck knitted sweater

With Knee-High Boots

Look super sophisticated this winter by styling a grey cardigan sweater over a turtleneck with a black mini skirt, black knee-high boots, and a long coat.

J.Crew Cable-knit cardigan sweater

Now 31% Off

& Other Stories A-Line Mini Skirt

With Shades of Red

I love wearing an outfit that features a few shades of a certain color. Try styling a red sweater with some burgundy pants and a scarf that ties in the color, as well.

Everlane The Classic Cardigan in Cashmere

Dailyacc Hair Bandanas Scarf for Women

Now 20% Off

Lucy Paris Adler Faux Leather Pants

Add Some Cheetah Print

We’ve seen cheetah print pretty much everywhere recently. Wear a black crewneck sweater with some cheetah-printed pants and add an oversized blazer.

Dissh Harley Black Oversized Boyfriend Blazer

Banana Republic Factory Perfectly Soft Crew-Neck Sweater

NA-KD Straight Leopard Denim

Over the Shoulders

With the unpredictable temperatures of the fall and winter, you gotta make sure you always have your sweater with you! If you get too warm, throw your sweater over your shoulders like this.

Sanctuary Perfect Tunic Pullover

Frame The Slouchy Straight

FAITHFULL THE BRAND En Vau Shirt

With Some Buttons

I’ve been obsessing over henley-style sweaters recently. Style it with a pleated skirt and some matching accessories.

Gap CashSoft Relaxed Polo Sweater

Ann Taylor Belted Pleated Midi Skirt

Now 30% Off

Alohas Sway Black Leather Ballet Flats

As a Mini Dress

You can easily wear an oversized sweater as a mini dress with knee-high boots. If the sweater isn’t long enough for comfort, throw on a mini skirt or a pair of shorts underneath! Finish the look with a matching bag.

Madewell The Dimes Kitten-Heel Knee Boot

Topshop knit high v-neck mini oversized dress

A Simple Blue Sweater

It’s always a good idea to have a simple blue sweater in your closet. You’ll get a lot of use out of this style—pair it with jeans for a casual, everyday look.

Pistola Denim Jadyn Low Slung Palazzo

Coconuts by Matisse Freedom Clogs

Devin Toolen is the Fashion Assistant at Cosmopolitan where she’s responsible for anything and everything that comes through the fashion closet doors. She preps ready-to-wear, accessories, and shoes for Cosmo photoshoots and assists on set. Devin also writes fashion stories for the Cosmopolitan website. Prior to Cosmo, Devin received her BA from Villanova University and her MA from Parsons in Paris, France. While she is passionate about fashion trends and current styles, she has a deep love for fashion history, heritage and archives. Follow her fashion journey on insta: @devintoolen.