25 Oversized Knit Sweaters to Get Lost in This Winter

Meet your new security blanket.

free people sweater

Free People / Design by Hallie Gould

While cold temperatures can sometimes take the pep out of your step, you must admit that your winter wardrobe can capture your personality. Yes, we love a puffer jacket, boots, gloves, and a thick scarf, but when it's cold outside, one of the first things that you think of is a warm and cuddly sweater. And if you can't think of a good reason to get one for yourself, they make a great gift during the holiday season. Below, 25 of our favorite oversized knit sweaters that can round out any look and help you to enjoy sweater season.

Modern Prep

Ribbed-Cashmere Oversized Turtleneck sweater
J.Crew Ribbed-Cashmere Oversized Turtleneck sweater $288.00

There is nothing plusher than cashmere, and this fine sweater from J.Crew is a standout. Its oversized turtleneck style is pure luxury. Tuck it into your favorite pair of wide-leg wool pants, and you have captured what hot chocolate feels like.


Oversized Merino-Cashmere Sweater
Banana Republic Oversized Merino-Cashmere Sweater $249.00

Banana Republic has always been about beautiful staple pieces that rarely go out of style, and this merino-cashmere sweater is a must-have. Stay warm and comfy by wearing a crisp white shirt beneath.

Cloud-Like Comfort

Oversized Funnel-Neck Sweater
Gap Oversized Funnel-Neck Sweater $69.95

Cool as ever is this oversized sweater from Gap. If you want to be warm but aren't a fan of a full turtleneck, this mockneck is perfect for you. Throw it on with your comfy boyfriend jeans, and you have a great weekend look.

The Perfect Tunic

Oversized Voop-Neck Cotton-Stretch Tunic Sweater
Old Navy Oversized Voop-Neck Cotton-Stretch Tunic Sweater $29.97

It is hard not to love a winter white sweater, and this cotton sweater is great for get-togethers this season. The best part about this neutral color is that it pairs well we every color in your closet. 

For Bold Layering

Oversized Cuffed Cardigan
Anthropologie Oversized Cuffed Cardigan $130.00

The best thing about a cardigan is how versatile it is, and this one can be worn over shirts, tanks, or tees.

Textured V-Neck

Long Ripped Knit Sweater
Zara Long Ripped Knit Sweater $49.90

A plush V-neck sweater like this one from Zara is the bold winter staple you need. It is perfect for days when you want to be casual but still look intentional.

Not Your Grandma's Cable Knit

Cable Knit Tunic Sweater
River Island Cable Knit Tunic Sweater $90.00

The best pieces of clothing are the ones that can do double—and sometimes—triple duty. This sweater dress does just that. It can be worn with a pair of tights and tall boots, over leggings, or belted on top of a midi skirt.

Neon Ballet Neck

Moira Oversize Ballet Neck Sweater
Free People Moira Oversize Ballet Neck Sweater $148.00

Free People understands the importance of stretch, and how it makes layering easy breezy. This oversized knit sweater with a ballet neck will help carry any outfit, but it would look exceptionally lovely with cigarette-style pant and your favorite flats

'90s Perfection

Oversized Turtleneck Sweater
Calvin Klein Jeans Oversized Turtleneck Sweater $79.50 $39.75

It can be trickc to find something to wear on casual Fridays, but this Calvin Klein oversized turtleneck will pair well with a pair of black skinny pants and slouch boots. 

Cozy Cowl Neck

Berry Cowl Sweater Dress
Taylor Jay Berry Cowl Sweater Dress $124.00

This Taylor Jay cowl neck sweater is just the sophistication you need to spice up your closet. Wear it with a pair of body-enhancing jeans for a fun night out with friends.

Autumnal Pullover

Space-Dyed Staley V-Neck Pullover Sweater
Madewell Space-Dyed Staley V-Neck Pullover Sweater $59.99

Madewell jeans are fantastic, and their sweaters are pretty cute too. Wear this with brown, beige, white, or blue denim for a casual Saturday afternoon look.

Classic Cardigan

The Texture Cotton Cardigan
Everlane The Texture Cotton Cardigan $110.00

A versatile cardi may not seem an automatic thought when looking for an oversized knit sweater, but they are a great way to take a fall dress into winter. They also work well in the spring when the temps are still a little cool.

The Coastal Grandmother

Women's Signature Ragg Wool Open Cardigan
L.L. Bean Women's Signature Ragg Wool Open Cardigan $129.00

A long button-less cardigan like this one from L.L. Bean begs to be belted and worn atop a blouse and a pencil skirt.

Oversized Glory

Camo Print Cowl Neck Tunic Sweater
Express Camo Print Cowl Neck Tunic Sweater $98.00 $58.80

While beige is a neutral color, it doesn't have to be boring. Try this camo print tunic sweater from Express with a bold pair of pants.

The Cabin Weekend

Soft & Cozy Mixed Stitch Sweater
American Eagle Soft & Cozy Mixed Stitch Sweater $59.95 $41.96

This pullover sweater can help you achieve a pulled together look for a weekend away with friends. Keep things simple and wear it with jeans.


Drip Sweater
Tyler McGillivary Drip Sweater $310.00

Stay dripping in this bright and bold paint drip sweater from Tyler McGillivary.

Relatable Colorblocking

"WTFIGO" Sweater
Rowing Blazers "WTFIGO" Sweater $295.00

Don't know? Then let it be known.

For Robe-Lovers

Waffle Belted Cardigan
Ann Taylor Waffle Belted Cardigan $109.00

Complete your office look with this waffle textured cardigan. It's versatility allows you to throw over a tank top or dress.

The Blair Waldorf

Carrie Sweater
Jakke Carrie Sweater $268.00

For the days when you have no idea what to wear, this can be your go-to choice. A cardigan? A sweater? Why not wear both?

Striped and Smiley

The Remus Smile
Kule The Remus Smile $398.00

For those extra dreary days when you just need some pops of color and a smiley face on your arm. This cashmere cardigan will do the trick.

If Money Is Your Favorite Color

Marcella Cardigan
Apparis Marcella Cardigan $150.00

If it's a little too cold for the ubiquitous green shirt, this cardigan will give you the same energy with some extra warmth.

Balloon Sleeves

Milo Pullover
Free People Milo Pullover $148.00

Balloon sleeves are quite the trend right now, but the drop shoulder with ribbed cuffs style of this Free People sweater is the relaxed version that will be a staple beyond this season. Find yourself some neutral-toned lace-up boots and pair them with beige-hued denim for a Sunday afternoon walk in the park. 

Striped Boucle

Stripe Boucle Sweater
Ashley Stewart Stripe Boucle Sweater $49.50 $24.75

A long cardigan is a chic way of skipping a jacket on a cool day. They keep you looking pulled together as well as toasty. Wear a knotted tee beneath with a cool pair of faux leather pants or leggings for a cool and casual look. 

Classic Turtleneck

Turtleneck Textured Wool Jumper
Nap Turtleneck Textured Wool Jumper $78.00

For those days when it is cold snowy outside you need full protection. This roll neck 100% wool knit sweater is just what you need to add as the warm layer over a long sleeved tee. Throw on your favorite pair of corduroys, Sorel Boots, gloves, scarf and puffer coat and you are ready to toss snowballs. 

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