The Coziest Oversized Sweaters That Will Keep You Warm All Winter Long

Photo: Stocksy / Jimena Roquero
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Ready or not, winter is officially here. Weather-wise, we're getting that chilly feeling, with temps dropping in the low 60s and 50s. It’s safe to say that most of us have already swapped our sweat-wicking fabrics for snuggly sweaters.

One trend that’s here to stay is oversized sweaters, but there's a new twist. Proportions are getting upsized for all categories, and sweaters are no exception, according to NYC-based stylist, Katya Bychkova. “With the 'clean-girl' aesthetic dominating our post-pandemic world, oversized bottom-ups and sweaters are everywhere,” she says.

Experts In This Article
  • Alison Bruhn, Alison Bruhn is a personal wardrobe stylist and the co-founder of The Style That Binds Us, a multi-platform fashion media company.
  • Grace Thomas, Grace Thomas is a Portland-based stylist and the founder of Builtgracefully, a personal styling company.
  • Katya Bychkova, Katya Bychkova is a stylist, beauty expert, and the founder and editor of Style Sprinter, a luxury blog dedicated to beauty, skincare, and fashion.
  • Laura Walters, Stylist + Founder, Style Riot, Laura Walters is a freelance personal stylist and founder of Style Riot, a personal wardrobe styling company.

Best oversized sweaters at a glance

Intentionally larger than a traditional sweater, these oversized varieties have a relaxed fit as opposed to a more tailored fit, explains Alison Bruhn, personal wardrobe stylist and co-founder of The Style That Binds Us. “It is so easy and quick to throw on an oversized sweater with a pair of jeans or leather leggings and boots,” she says. “The look is modern, doesn’t have to be ironed, feels wonderful on, and is moving us in the direction of finding our way stylishly into the new normal as we bravely go forth into the unknown territory of life after COVID.”

What to look for when shopping oversized sweaters

When shopping for an oversized sweater, here are a few features that’ll make your look standout amongst the crowd.

1. Pick timeless prints and colors

Consider investing in sweaters that are made in prints and colors that will last through the years—i.e. camel, winter white, black, brown, and beige. Laura Walters, stylist and founder of Style Riot, recommends thinking of less distinct prints and more neutral shades that will withstand the test of time.

2. Make sure it's the proper length

The right oversized sweater length depends on whether you are planning on tucking it or not, according to Bychkova. “The ideal sweater length for a ‘fashion tuck’ trick is mid-thigh,” she says. “If you plan on wearing your sweater out, you can go as long as above-the-knee length.”

3. Be choosy with fabric

Personal wardrobe styling company based in Portland, Oregon, Grace Thomas, recommends considering what type of material will work best for you and how you might be wearing the sweater. “If you're in a location that tends to run a bit warmer in the winter, a lightweight cotton blend sweater would be ideal,” she says. “If you’re looking for something that can get you through cold winters, opt for a wool blend, which will provide the most warmth.”

4. Don’t size up

An oversized sweater doesn't equal a sweater that is too big on you. “If the style allows and you could fold the sleeves nicely, you could pull off wearing a sweater a few sizes bigger than you need, but if the silhouette of a regular sweater is too figure-hugging and has a print, it's more challenging to make a traditional sweater look like a stylish oversized model,” warns Bychkova. “Look for an oversized sweater at the men's department instead: typically such options are longer which is ideal for channeling that oversized fit.”

5. Check the shoulder seam and sleeve length

One of the main features Thomas looks at when shopping oversized sweaters is the shoulder seam. “Many of these styles feature a drop shoulder, meaning the seam falls lower on your arm rather than at the top of your shoulder, which is great for those on more of the petite end of things or those with narrow shoulders,” she says. However, if you're looking for a style that’s oversized but still tailored, she suggests making sure the shoulder seam sits at the top of your arm.

Sleeve length is also key. “If your sleeves are too long, you won't look as put together, so you want to either roll up the sleeves until they hit right at your wrist or hire a tailor to trim a few inches off,” she says. “These small details will make your oversized look still look polished.”

But also? There are no rules! Wear your oversized sweater however you wanna—the most important thing is that you're cozy, cozy, cozy.

Best Oversized Sweaters

cable cocoon
Best Cardigan: Jenni Kayne Cable Cacoon Cardigan — $425.00

Sizes available: XS-XL
Colorways: Ivory, black, blush, sand, charcoal

Jenni Kayne’s best-selling cardigan is chunky, oversized autumnal Tumblr heaven. It’s a splurge, but it’s well worth it. Not only will its high-quality material last you years and years, but its neutral colors will go with just about everything you own. Made with a blend of baby alpaca, merino wool, and nylon, it’s just as soft as it is toasty, and it’s even got a bit of stretch. While it’ll keep you warm, it’s not heavy at all, so it’s perfect for layering. Buy it now before it sells out—this happens every year, so we wouldn’t wait if we were you.


Best cashmere: Quince Mongolian Cashmere Batwing Sweater — $80.00

Sizes available: XS-XL
Colorways: Heather Grey, Everglade Green, Navy, Oatmeal, Burgundy, Black, Spicy Mustard

Everyone deserves a new cashmere sweater each cold-weather season, and we’re loving this oversized style from Quince. Made from 100 percent grade-A Mongolian cashmere, it features an oversized fit and slouchy batwing arms to give it some edge.

Best turtleneck: Rag & Bone Ingrid Stitched Turtleneck Sweater — $371.00

Sizes available: XXS-XL
Colorways: Dark brown, ivory

This gorgeous, turtleneck sweater features drop shoulders, long sleeves and a pullover style with the sleeve detailing being the real showstopper. “A perfect piece to wear with a pair of plaid pants or a relaxed denim,” says Walters.

Best sweater vest: Banana Republic Cima Oversized Sweater Vest — $50.00

Sizes available: XXS-XL
Colorways: Pale Khaki, Navy, White

If you’re digging the coastal grandmother trend and want to try it out, this sweater demands a spot in your wardrobe. You can dress this classic piece up or down, or easily layer it over a crisp white button down and tuck it into high-rise, wide-leg khaki pants, according to Walters.

& Other Stories Mohair Sculpted-Sleeve Jumper
Best mohair: & Other Stories Mohair Sculpted-Sleeve Jumper — $134.00

Sizes available: XS-L
Colorways: Green

Green is having a serious moment—and the trend is expected to carry its way into the season. Not only is green bold, joyful and makes a statement, but you can wear it in a super on-trend monochromatic way, or tone it down a little with a jean, explains Bruhn. This responsible mohair wool sweater is perfectly billow-y, featuring subtle sculpted sleeves.

Best ribbed: Anine Bing Sydney Sweater — $350.00

Sizes available: XS-L
Colorways: Camel

If you’re a fan of the half-tuck look with a chunky sweater, Bruhn recommends pairing with some high-waisted jeans and a nice pump heel. The material is so soft and snuggly and runs true to size, so be sure not to size up!

Cos V-Neck Patch-Pocket Cardigan
Best with pockets: Cos V-Neck Patch-Pocket Cardigan — $101.00

Sizes available: XS-L
Colorways: Beige, Navy

In a neutral beige shade, as well as a deep, dark navy, Walters loves this fun, whimsical and feminine cardigan. She recommends wearing over a tee-shirt and black leather pants or dressing it up a bit with a belt, houndstooth skirt and white knee high boots.

Best balloon sleeve: Lulus Always Together Balloon Sleeve Sweater — $52.00

Sizes available: XS-XL
Colorways: Mauve Purple, Forest Green, Brick Red

In-line with the puffed-sleeve theme surrounding dresses earlier this year, we’re loving this balloon-sleeved sweater. It is made of a fuzzy marled knit with a wide rounded neckline and drop shoulders. The ribbed accents around the neck, cuffs and hem make it a great option to pair with some high-waisted jeans and a bold ankle bootie.

Best tunic length: Free People Easy Street Tunic — $128.00

Sizes available: XS-XL
Colorways: Cream, Black, Heather Grey, Painted White, Green Light

This ribbed mock pullover hangs low at a tunic length, which makes it great for pairing over a comfortable pair of leggings for a low-key look or dressing up with a bootleg pair of jeans and some heels for a night out.

Best drop shoulder: Autumn Cashmere Oversized Turtleneck — $375.00

Sizes available: XS-XL
Colorways: Black

“A key detail to note on this sweater is the dropped shoulder, this is the seam on the garment that is positioned on the upper arm rather than the shoulder,” says Melina Kemph, New York-based fashion stylist.

“The classic turtleneck with a looser fit makes this sweater an easy go paired with jeans, trousers, even thrown over a dress/skirt…business casual or dressed up the versatility is endless.” She recommends sizing up to make the dropped shoulder seam fall closer to the elbow.

Everlane The SuperFuzz Alpaca Oversized Crew
Best alpaca wool: Everlane The SuperFuzz Alpaca Oversized Crew — $138.00

Sizes available: XXS-XL
Colorways: Heathered charcoal, Dijon, Seafoam Green, Turmeric Stripe

Oversized and fuzzy, this alpaca wool sweater is warm , without the itch. It’s made with a blend of alpaca wool, merino wool, and nylon, to give it an ideal blend of softness and stretch. It has an easy-to-wear crew neck, blouson sleeves, and ribbed cuffs and hem. It goes great with jeans, but you can also dress it up for those cold nights out.

ASOS Design Mock Neck Oversize Sweater
Best mock neck: ASOS Design Mock Neck Oversize Sweater — $48.00

Sizes available: 0–14
Colorways: Pink

When it’s cold and dreary outside, sometimes the antidote is to add a pop of color to your day and outfit. This pink sweater will keep things warm and fun, with its fuzzy fabric and fun, blouson sleeves. It also has a mock neck to give you a little extra coverage.

Naadam Merino Cashmere Cable Turtleneck
Best cable knit: Naadam Merino Cashmere Cable Turtleneck — $250.00

Sizes available: XXS–XXL
Colorways: White, Black, Marley Gray

This turtleneck is made from a soft wool/cashmere blend, but what sets it apart are all the fine details. It has a roll neck collar you can wear up or down, and the sleeves have a textured, cable knit design that’s subtle and stylish. A ribbed hem and cuffs finish it off for a polished look no matter what you pair with it.

Reformation Cashmere Boyfriend Sweater
Best striped: Reformation Cashmere Boyfriend Sweater — $119.00

Sizes available: XS–XL
Colorways: Camel Stripe, Camel/Gossamer Stripe, Chestnut, Gossamer/Black Stripe, Gigi, Gossamer/Postbox Stripe, Light Grey, Nectarine

Made of 90% recycled cashmere and 10% virgin cashmere, this sweater has 87% less carbon impact than conventional cashmere, so you’ll feel good about making this your go-to sweater. It has a relaxed fit, ribbing at the cuffs, and hems, and plenty of stripe options for those looking to add some pattern to their closet.

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