All sizes in this post are listed in women’s, unless stated otherwise.
1. A flared Peter Pan collar dress for those who see Wednesday Addams as their fashion muse, even when it's not Halloween.


2. A chic sweatshirt dress with a diagonal side zipper, perfect for when you want to feel cozy and still look fabulous.


Marcella is a boutique in NYC founded by two sisters who craft minimalist yet edgy designs. When you buy their pieces, you're helping fund the education of a girl in Africa for three days through their partnership with CAMFED.org.
Raving review: "This is the perfect casual dress — especially for chilly days. The fabric is thick and durable, with extra-long sleeves, and the zipper adds a modern, sexy flair." —Marilyn LaVergne
Another glowing review: "I adore this dress, it's ideal for winter. The material is thick and cozy, and I love the hand loopholes." —Meg Skelton
Available from Marcella on Etsy for $98 (sizes XS–XXXL, available in three colors).
3. A luxurious velvet maxi with an adjustable waist tie belt, just in time for the holidays, which are approaching fast. You're definitely going to need a new party dress, right? Those jewel-toned colors are the perfect festive touch!


4. A cozy button-down cardigan dress, resembling your favorite grandpa sweater but with a more polished twist. The long length will keep your legs warm, and the adjustable sash lets you choose between a fitted or relaxed look.


Raving review: "This cardigan sweater dress is AMAZING!!! It's just as thick and cozy as I hoped for fall/winter. I bought both colors. I plan to wear it as a dress or open over jeans." —Joy
Another glowing review: "I love the fit and the color. It’s warm and doesn’t itch. It ran true to size." —Ladytee77
Available from Eloquii for $129.95 (sizes 14–32, in brown or green — not all sizes available in both colors).
5. A scoop-neck sweater dress featuring the cutest side buttons, giving off major "I'll be relaxing at a cozy ski lodge with hot cocoa while you’re skiing down the slopes!" vibes.


6. A sporty tunic dress that I’m confident will quickly become your favorite this season due to its versatility. The subtly puffed sleeves elevate it beyond your everyday sweatshirts, and it pairs perfectly with both flats and sneakers.


Promising review: "It’s so cozy and comfy, making it the perfect casual tunic to wear over leggings for cool weather or chilly evenings." —lanilee
Get it from Anthropologie for $98 (available in regular sizes XXS–XL, petite sizes XS–XL, and plus sizes 1X–3X in gray, with additional colors in standard sizes).
7. An effortlessly chic V-neck maxi that’s both stylish and low-maintenance. The slip-on design is super easy, and the lacy long sleeves offer extra warmth while staying breathable.


8. A polo sweater dress that adds a touch of prep to your wardrobe, featuring a sharp collar and a sleek look. Perfect for pairing with your loafers!


Promising review: "Absolutely love this dress! It's the perfect combination of cozy and cute. It's thick enough to keep me warm, but not too thick, making it ideal for fall weather. While many reviews suggest sizing down, I went with my usual size and it fit perfectly." —Taylor Canty
Get it from Target for $35 (available in sizes XS–4X in brown or gray).
9. A long-sleeved maxi dress that even those who say they "don’t like dresses" will love. Once you feel how comfortable it is, you'll see why—it’s like wearing a nightgown, but socially acceptable outside the house.


10. This vibrant striped sweater dress will infuse a splash of color into your fall or winter wardrobe, which is often dominated by neutral tones. Wearing these beautiful shades guarantees a joyful vibe!


Highly recommended review: "I paired this sweater dress with my go-to Torrid leggings. It's incredibly cozy, warm, and the colors are wonderfully bright." —RJ0325
Get it at Torrid for $76.07 (regular price $89.50; available in sizes M–6X, with limited black size options).
11. This preppy mod pencil dress is perfect for the holiday season, especially with its classic plaid pattern. The long sleeves are perfect for chilly days, and it pairs beautifully with chunky ankle boots.


12. Try a plaid tunic that will have you feeling like the most fashionable lumberjack, even if you've never picked up an axe. If this doesn't make you want to cozy up by a fire, I don't know what will!


Highly recommended review: "I tried it on, and it fit perfectly, and felt like a warm, soft blanket enveloping me. It will be ideal when the chilly weather hits." —Kathy C.
Get it from Faherty for $188 (available in sizes XXS–XXL in two plaid patterns, plus three solid color options).
13. This cocoon-style pullover hoodie dress is like a shortcut to looking effortlessly chic with minimal effort. The color choices are fantastic! Pair it with leggings or tights for the coziest cold-weather look.


14. This lantern-sleeve mini dress is the perfect pairing for your thigh-high boots when the temperatures start to drop. A touch of glamour, 100% comfort.


15. A chunky button-neck dress that brings a bit of asymmetric flair to our wardrobes! If you love the snugness of a turtleneck but want some extra room to breathe, this dress is the perfect choice.


16. This ethereal, flowing maxi dress features the most charming pleats at the waist, making it stand out from all the other basics in your wardrobe. Made from a breathable cotton-linen blend, it'll keep you warm without overheating.


Designer Yao is a small business based in China that specializes in creating custom clothing using linen-cotton blend fabrics in the most beautiful colors.
Promising review: "This dress is perfect for autumn! It keeps me warm without being too heavy, and the color is absolutely stunning. I feel like a pumpkin-spiced version of myself. I got it in a custom size, and it fits perfectly. The shop owner even sent a matching belt! :) And let me tell you, pockets! I'm completely in love with this dress and I'm already placing an order for two more from this designer." —detgirl
Get it from Designer Yao on Etsy for $113.49+ (available in sizes XS–6XL, as well as custom sizes, and in 30 colors).
17. This fuzzy crewneck mini is *almost* as cozy as cuddling with your cat. You can dress it up with tall boots, or go for a casual vibe with leggings and sneakers.


18. This purr-fect leopard-print maxi features cozy long sleeves and everyone's favorite detail: pockets! If leopard print isn't your style, don't worry—this dress comes in a variety of beautiful floral prints and solid colors to rock this season.


19. This fitted ribbed midi comes in 18 stunning colors, and once you see how chic it looks and how incredibly comfortable it feels, you’ll want to own one in every shade. The ultimate combo of style and comfort!


20. This utterly stylish ruched thermal dress is nothing short of genius. It’s incredibly cozy for cold weather and still looks fabulous. Pair it with your favorite combat boots for the perfect look. *Chef’s kiss*


Promising review: "This dress is beautiful, and the style is one-of-a-kind. The softness and warmth are just amazing. I ordered a size up for extra comfort and to wear while lounging or sleeping. It reaches just above my ankles, and I’m 6’0!" —Lanikai
Purchase it from Free People for $128 (available in sizes XS–XL and six colors — not all colors are available in every size).
21. This super cozy wrap sweater dress is the perfect match for a hot PSL, the ultimate cold weather accessory. If you told me it cost three times as much, I'd totally believe it.


22. This slouchy turtleneck midi is for anyone who’s ever wanted to wrap up in a cozy blanket all day. Now, you can, while still looking chic as ever!


23. This breathtaking pleated sweater maxi looks far more expensive than its under-$50 price tag! The vibrant skirt paneling and shoulder details add so much charm to the dress.


Vogue by Nekar is a small business operating between China and New York, known for its handmade jewelry and other fun accessories. They suggest sizing up or referring to their size guide for the best fit.
Promising review: "This is my first time buying clothing on Etsy. I was nervous, but there was no need! It fits perfectly and looks just like the pictures! The material is so warm, perfect for fall and winter! The skirt’s colorful section is made of thick pleated material, the same on the back. Half the skirt is pleated, and the other half is cozy winter material. Super soft and comfortable. My favorite dress so far! The sleeves are a great length, and it hits mid-calf on me. True to size!" —Maria
Get it from Vogue by Nekar on Etsy for $47.99 (available in sizes S–XL and four colors).
24. A cute tie-front mini that you'll be glad you picked up when holiday party season comes, as you can dress it up with heels and jewelry without compromising comfort.


25. This soft, 100% cotton sweater tunic is incredibly low-maintenance, providing that stylish layered look without the need for multiple pieces. Just add tights and boots, and you’re good to go.


Maya Antonia Design is a small business based in Corona, California, founded by a mother-daughter duo with a mission to create high-quality, affordable clothing.
Promising review: "Cute and comfy dress, perfect for winter!" —DANIELE
Another promising review: "I received this dress just days after ordering it and it’s exactly as shown. It’s adorable and well-made. Highly recommend this shop. Thanks so much." —Amy
Get it from Maya Antonia Design on Etsy for $68+ (available in sizes M–2X and in black or green).
26. A textured cable-knit mini, perfect for when you want to look polished without sacrificing the comfort of your pajamas. Throw on a bold shoe and handbag, and no one will guess you got dressed in under five minutes.

27. This highly-rated oversized turtleneck dress has over 12,000 five-star reviews, so it’s clearly a favorite! The looser fit is trendy, but if you prefer a more tailored look, it pairs beautifully with a waist belt.


28. This cozy hooded jacket-dress hybrid will keep you warm on those extremely cold days when you just want to stay tucked in on the couch. It’s like a sleeping bag you can wear!

AnySize is a small business that creates beautifully tailored pieces designed to fit, as their name suggests, any size!
Promising reviews: "Soft, cozy, and perfect for the coldest nights. I ordered this with a few extra inches added to the length and now I’m toasty warm all the way to my toes! Thank you for yet another fantastic purchase!" —M E
Get it from AnySize on Etsy for $162.70+ (available in sizes S–6XL and 69 colors — you can even provide your measurements for a custom fit). A longer length version is also available here!
29. A breezy ribbed mini dress for anyone who loves a bold sleeve statement! The balloon sleeves make this sweater dress feel extra plush, and it’s perfect for both going out or just relaxing at home.


30. A super cozy terry dress that many reviewers love to wear as a nightgown, but it's stylish enough to wear out while running errands or hanging out with friends.


31. A V-neck maxi featuring a gently ruffled skirt, perfect for both dressing up and down. Whichever way you wear it, you'll love living in this comfy piece. Plus, the cute slit adds a cheeky touch!


32. This elegant crewneck midi is a must-have, especially when paired with your go-to leather jacket for a chic layered look. It’s also the ideal length to showcase those ankle boots you scored during fall Prime Day.


Promising review: "It fits perfectly without being too loose anywhere. The neck is a bit tight initially, but once on, it looks amazing. It's heavy, so it's perfect for winter. I love the color and style." —Carol
Get it from J.Crew for $228 (available in sizes XXS–3X).
The reviews in this post have been shortened and clarified for readability.