As a fashion gal, I admit that fall and winter are probably my favorite seasons for style. As the temperature cools down, you will be able to layer your clothes. One of the most important elements of layering is wearing a good sweater. Sweaters can be styled with literally anything you have in your closet. You can pair it with jeans, work pants for a casual look, a skirt for a night out with friends, or even sweats for lounging around the house.
Now, you may already have some sweaters in your closet. Or maybe you want to invest in a new sweater for winter. Anyway, I’d like to help you understand how to look effortless when wearing them! Below, I’ve compiled 21 great street style sweater outfits. There are many different styles, including formal, casual, sweater dresses, and sweater vests. Use this as inspiration for your next sweater outfit, or treat yourself to a new item for the colder months. Enjoy shopping, friends 🙂
simple cardigan
jeremy moeller
A simple cardigan is great for the cold season. Wear it with button-up, low-rise baggy jeans and sleek, pointed-toe kitten heels.
Aritzia Cashmere Relaxed Crew Cardigan Garage Low Rise Baggy Jeans Mark Fisher Iggy Dress Booties
cropped look
edward bertolo
PSA: You don’t have to buy a cropped sweater to wear a crop top. Simply tuck the sweater into your bra to complete this look. I promise you’ll get a lot more use out of a full-length sweater than a cropped one.
Australian Merino Wool Cable Sweater
Now 82% off
Paksan Seaweed Cargo Dad Pants
Now 52% off
Circus NY Tara Slingback Heel
in a miniskirt
jeremy moeller
This fall/winter, pair an oversized cardigan with a cute miniskirt and Mary Jane flats. Don’t forget tights if your feet get cold!
LILLUSORY Women’s Oversized Cardigan Sweater Antonio Melani Rose Houndstooth High Rise A-Line Mini Coordinating Skirt Sam Edelman Michaela Mary Jane Flat
Incorporate prints and graphics
Daniel Zuchinik
It’s always fun to add prints and patterns to your style. Try pairing a graphic sweater with a neutral-colored skirt and a cute bag that complements the sweater’s color.
Ralph Lauren Intarsia Knit Dachshund Sweater Los Angeles Apparel Tennis Skirt Small Stella Texas Braid Dark Brown
wide leg jeans and
edward bertolo
Style your bright yellow sweater with comfortable wide-leg jeans and black boots. It’s a simple costume, but it’ll work!
Good American Good Ease Relaxed Jeans AMY LYNN Chelsea Yellow Leather Tote Bag
sweater vest
Claudio Lavegna
Sweater vests are the perfect layering item. You can choose long sleeves, short sleeves, or tanks underneath. Or, on warmer days, style a sweater vest without an undershirt. For a cool girl look, pair a sweater vest with a long denim skirt and cute ballet flats.
Ganni Multicolor Striped Vest BLANKNYC Denim Skirt (Black)
chosen by professionals
Claudio Lavenia
If you want to wear a sweater in a more professional setting, try pairing a simple black crew neck with pants and a long coat.
Gap 365 High-Rise Brushed Twill TrousersEverlane The Boxy Sweater in Everyday CottonAllSaints Mabel Double-Breasted Coat
floral cardigan
edward bertolo
Keep your outfit fun and colorful by styling it with a floral cardigan and matching pants.
Madewell The Emmett Wide Leg Pant in Corduroy: Welt Pocket EditionBLANKNYC Flower Cardigan (Sweet Soulhana) Medium Faux Suede Tote Bag – Brown
with metallic pants
Raymonda Krikauskine
Metallic pants were one of the biggest fashion trends a few seasons ago. If you own a pair or are interested in styling them yourself, try wearing them with a white sweater and white accessories. This fit is perfect for the upcoming holiday season!
Levi’s 501 90’s ankle jeans
sweater dress
Claudio Lavegna
For an easy outfit, pair a long sweater dress with a simple black bag and sunnies. If the weather is cold, choose closed-toe heels or boots.
Brandon Blackwood Luna Zip Leather Shoulder Bag Reformation Revere Regenerative Merino Sweater Dress Elisa Johnson Cookie 54mm Cat Eye Sunglasses
V-neck sweater
Daniel Zuchinik
I want to enjoy the moment of being ready! To achieve this look, pair a V-neck sweater with a pleated miniskirt.
Lacoste Women’s V-Neck Cable Knit Cotton Tennis Sweater
50% off now
TONCHENGSD Women’s High Waist Pleated Mini Skirt Skater Tennis Skirt Vans Old School Pig Suede Shoes
Now 31% off
monochrome look
Christian Vierig
I love monochrome outfits like this. Try styling a black sweater with faded black jeans, a black bag, and kitten heels.
NA-KD Turtle Neck Knit Sweater We The Free Tinsley Baggy High Rise Jeans Schutz Women’s Loose Decoration Slingback Pumps
maxi skirt and
Mauricio Santana
Styling it with a striped sweater and maxi skirt will keep you cozy and cute even in cold weather. Finish your look with a comfortable chuck.
Hill House Home The Delphine Nap Skirt Z Supply Black Josephine Striped Turtleneck
Add bold accessories
Daniel Zuchinik
Bold accessories can make any outfit more interesting. Next time you think your outfit is a little plain, try adding some color with a bold scarf!
Free People Stripe Hair ScarfMango Round Neck Knit Sweater
With knee high boots
jeremy moeller
Look super sophisticated this winter by wearing a gray cardigan sweater over a turtleneck and pairing it with a black miniskirt, black knee-high boots, and a long coat.
J.Crew Cable Knit Cardigan Sweater
Now 31% off
& Other Stories A-line mini skirt
in shades of red
Valentina Furjuele
I love wearing clothes that incorporate several shades of a particular color. Try styling a red sweater with burgundy pants and a scarf of the same color.
Everlane Cashmere Classic Cardigan Dailyacc Hair Bandana Scarf for Women
20% off now
Lucy Paris Adler Faux Leather Pants
Added cheetah print
Valentina Fuljuele
Lately, I’ve been seeing cheetah prints everywhere. Wear a black crew neck sweater and cheetah print pants and pair it with an oversized blazer.
Dish Harley Black Oversized Boyfriend Blazer Banana Republic Factory Perfect Soft Crew Neck Sweater NA-KD Straight Leopard Denim
over your shoulder
edward bertolo
Temperatures are unpredictable in fall and winter, so you should always carry a sweater with you. If it gets too hot, just throw the sweater over your shoulders like this.
Sanctuary Perfect Tunic Pullover Frame The Slouch StraightFAITHFULL THE BRAND En Vau Shirt
with some buttons
Daniel Zuchinik
Lately I’ve been into henley neck sweaters. Style it with a pleated skirt and matching accessories.
Gap Cash Soft Relaxed Polo Sweater Ann Taylor Belted Pleated Midi Skirt
30% off now
Alohas Sway Black Leather Ballet Flats
as a mini dress
Mauricio Santana
You can easily wear an oversized sweater as a mini dress with knee-high boots. If the sweater isn’t long enough, wear a miniskirt or shorts underneath. Complete your look with a matching bag.
Madewell The Dimes Kitten-Heel Knee BootTopshop Knit High V-Neck Mini Oversized Dress
simple blue sweater
edward bertolo
Keep a simple blue sweater in your closet. This style is versatile and can be paired with jeans for a casual everyday look.
Pistola Denim Jaydin Low Slang Palazzo Coconut by Matisse Freedom Clogs
Devin Toolen is a fashion assistant at Cosmopolitan and is responsible for everything that comes through the fashion closet door. She prepares ready-to-wear, accessories, and shoes for Cosmo’s photo shoots and helps set them up. Devin also writes fashion stories for the Cosmopolitan website. Prior to joining Cosmo, he earned a bachelor’s degree from Villanova University and a master’s degree from Parsons in Paris, France. While she is passionate about fashion trends and current style, she also has a deep love for fashion history, tradition, and archives. Follow her fashion journey on Instagram: @devintoolen.
