Unless otherwise specified, all sizes in this post are listed in women’s.
1. A cable knit chunky pullover sweater you can totally get away with wearing as a dress or with leggings — add in your favorite over-the-knee boots for a fabulous lil' look.
2. An oversized pullover V-neck sweater made of a cozy waffle knit material you won't be able to get enough of — it'll look just as cute with leggings at home as it will with your fave pair of denim.
Promising review: "I ordered a size up because I wanted a really loose fit. I'm a normal medium and got a large. It is really great to wear with leggings and makes you look like a cute, cuddly, snow bunny. I've bought a second one already and I'm looking at a third." —Nikki S. Kitchen
Get it from Amazon for $26.99+ (available in sizes S–2XL and in 24 colors).
3. An oversized crewneck sweater you can comfortably wear with leggings on busy WFH mornings where you want to feel cozy but still be a little dressed in case you have to hop on a Zoom call.
I bought this sweater and it's fantastic — super stretchy but cozy at the same time. I've been wearing it with leggings (the medium is long enough on me, I'm a little over 5 feet tall) but can totally see wearing it with jeans as well! It's washed beautifully (no pilling) and I will definitely buy more colors.
Promising review: "This is a great loose fitting sweater. So comfortable. Great to lounge around the house in sweats or throw on some leggings or jeans and run errands. I wear it a lot." —Michelle S.
Get it from Amazon for $24.99+ (available in sizes XS–XL and 29 styles).
4. An oversized knit cardigan in an array of gorgeous colors — ideal if you're someone who *waffles* between being too hot and too cold and loves nothing more than a go-to layering option.
Promising review: "I followed the advice of other reviews and bought up a size so that it would be baggy and comfortable, and this cardigan quickly became my favorite to wear. Perfect to wear with leggings, really comfortable material against the skin. Definitely recommend!" —Brittany Kingan
Get it from Amazon for $42.99+ (available in sizes S–3XL and 29 colors).
5. An open-front blanket shawl you can claim is *~fash-hun~* but in reality we both know you're just wearing it to feel like you're actually still lying in bed watching re-runs of Seinfeld.
Promising review: "This sweater poncho is so cozy and thick. It’s perfect for the fall! I grabbed this while I went on my trip and it kept me warm on the airplane. I’m glad I grabbed it because it was freezing on the airplane! It’s super cute paired with leggings and boots." —MJ
Get it from Amazon for $32.99+ (available in 29 styles).
6. A soft sweater, so cozy you'll want to buy 10, cut 'em all up, and make a blanket out of them. But, like, don't do that.
Promising review: "I love this sweater! I bought it to wear with leggings to work and it is the perfect length to cover everything while wearing leggings. It is also very warm and soft! " —Rebecca Gerstorff
Get it from Amazon for $38.99+ (available in sizes S–2XL and 13 colors)
7. A turtleneck pullover with a unique coloring that'll make it seem like you really *tried* to get dressed-up.
Promising review: "This product is soooo cute! It is surprisingly high quality and looks high end for the price. The structure is comparable to more mid range sweaters I have! The fit is baggy and oversized, which is perfect for wearing over leggings or for tucking into jeans. Would totally recommend this product! It’s an absolute steal for the price!" —G4
Get it from Amazon for $27.99 (available in sizes S–L and four styles).
Psst: This item is included in Amazon's Try Before You Buy service, so you can give it a trial run if you're a member!
8. A chic sweater starring an asymmetrical hem, long enough to cover your booty so you can wear your leggings without hearing "those are NOT pants, I can see your whole butt!"
Promising review: "Ordered a small in the white version of this sweater and holy cow! I intend to buy this in black as well, so impressed. This sweater is incredibly soft and stretchy and comfortable. It does run slightly large in my opinion, however, I wouldn't order a size down. This has been washed several times since I ordered it and I am impressed with how it's held up. 10/10 would recommend to a friend! Great value for the money spent." —Elizabeth
Get it from Amazon for $45.99+ (available in sizes XS–XL and 29 styles).
Psst: This item is included in Amazon's Try Before You Buy service, so you can give it a trial run if you're a member!
9. A cable knit sweater featuring a split hem and a turtleneck to keep you nice 'n' toasty at all times — it's super oversize so if you want a more fitted look you best go down two sizes.
10. An oversized cardigan with contrasting stripes for a cool, collegiate look you'll definitely want to add to your closet.
Get it from Boohoo for $18 (originally $35; available in sizes 12–24 and three styles).
11. A bat-wing sweater complete with a stylish hollow knit that'll make it stand out from all the other sweaters in your closet.
Promising review: "Perfectly oversized, great for a slouchy off-the-shoulder look. Could wear with leggings as it covers your butt. I’m wearing just a nude shelf bra under mine — you’d need a tank or something as you can see through the 'holes.'” —Megan
Get it from Amazon for $35.99+ (available in sizes S–XL and six colors).
12. A super-soft cardigan you can wrap yourself up in on rainy or snowy days so you can feel like you're home snuggled in a blanket even when you're not.
Promising review: "Nice oversized cardigan. Warm and has pockets! Works great for cool summer nights under a tank or in between layers during fall and winter months. Size down if you want this to be more fitted." —Becky Wolz
Get it from Amazon for $39.99 (available in sizes S–2XL and 31 styles).
Psst: This item is included in Amazon's Try Before You Buy service, so you can give it a trial run if you're a member!
13. An oversized number starring an alpaca/Merino wool blend, a loose turtleneck, and extended length in the back (2 extra inches!) to ensure you can comfortably wear them with those faux-leather leggings you've been itching to try out.
Rose Unique Style is a small business based in Toronto, Canada that sells gorgeous handmade sweaters.
Promising review: "Premium quality, matches description, meets expectations. I like it so much that I also ordered the same in chocolate brown! Gorgeous yarn, gorgeous knitting! Feel like a million dollars! Let it snow!" —Michele Fairfield
Get it from Rose Unique Style on Etsy for $124+ (available in sizes S–3XL and four styles).
14. A long cable knit cardigan for anyone who is actually VERY bothered by the cold (unlike Elsa, of course) and will do anything to feel warm 'n' cozy this winter.
Promising review: "The long length along with buttons help during cooler weather to keep the chill off me. I love the color, true navy, and the cable knit stitching adds style. It will look good with leggings or jeans as well as dresses." —Darlene Williamson
Get it from Amazon for $43.99 (available in sizes S–2XL and 30 colors).
15. A fuzzy V-neck popcorn sweater you'll find yourself as infatuated with as the smell of the freshly popped snack.
Promising review: "This is my favorite new sweater! The quality is amazing! It's super soft and the color is a pretty taupe that goes well with everything. It's definitely oversized, so order your normal size. I love the detail on the sleeves and the length is great. I'm tempted to buy the other colors now!" —Laura Chaffee
Get it from Amazon for $23.99+ (available in sizes S–XL and 15 colors).
16. An oversized sweater that can only be described as "fiiiiire" — it's unique and definitely deserves a spot in your winter wardrobe.
Promising reviews: "I have this in four colors lol. It’s a nice thick weave and it hasn’t fallen apart. I purchased my first one over a year and a half ago, wore it almost every day for like six months, and it’s still in perfect condition. No problems with machine washing and it’s not itchy or anything." —Erin
"I was a little hesitant because it was so cheap but NO this sweater is so comfy and warm and I'm L I V I N G." —Matthew Pauletich
Get it from Amazon for $32.99 (available in one size fits some and 12 colors).
17. A splurge-worthy oversized alpaca cardigan to prove once and for all you can be both chic and cozy at the same time. Good luck convincing yourself you don't need to buy at least three. 😅
Get it from Everlane for $178 (available in sizes 2XS–XL and five colors).
18. A chunky turtleneck, because even if you already own a plethora of sweaters you're not going to be able to resist adding this snuggly beauty into your collection.
Promising review: "I love this sweater. The price point is great. Super cozy and is perfect for the fall/winter season. This sweater would look perfect with a pair of distressed jeans and a cute fedora hat." —Tracy Fletcher
Get it from Amazon for $25.99+ (available in sizes XS–XL and in eight colors).
19. A linen sweater that'll give you the option of donning the style of thick, knit sweater but without all the sweating that goes along with it if you're someone who is *always* hot (ahem, me).
Bliss Linen is a Lithuanian small business on Etsy that sells a variety of linen clothing and accessories.
Promising review: "Oh my god, this exceeds all my (very high) expectations! It's PERFECT! Absolutely gorgeous as well as lightweight and soooo comfortable. I'm ecstatic." —Sibylle Leon
Get it from Bliss Linen on Etsy for $129 (available in sizes XS–3XL and six colors).
20. A chunky knit cardigan that's basically the winter version of the "Make it pink! Make it blue!" conundrum from Sleeping Beauty — except a compromise has clearly been made to include both fabulous shades in one gorg piece.
Beginning Boutique is a woman-owned small business based in Brisbane, Australia, that sells an array of gorgeous apparel.
Get it from Beginning Boutique for $104.99 (available in sizes XS/S and M/L).
Reviews have been edited for length and/or clarity.