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1. A leopard-print button-down midi with a drawstring waist to brighten those dark and dreary winter days. Add a pop of color and bold print with this gorgeous dress that you can wear with boots and a chunky cardi in the winter, then transition into spring with a cute pair of flats.
2. An oversized turtleneck sweater dress that checks all the boxes. Cute: yes. Versatile: totally. Comfy: oh so comfy. Wear it with or without a belt, pair it with ankle or OTK boots — this soft and stretchy dress will look good every time.
3. A scalloped off-the-shoulder swing dress for some serious Midge Maisel vibes. The boat neckline, fitted top, and full skirt give it an elegant retro vibe that'll make you feel marvelous the second you slip it on!
4. A chic mock-neck grid-patterned pullover dress that looks like it cost way more than $50. Wear it with tights and your favorite boots to stay warm on those frigid days when you don't even want to open your weather app.
5. A warm knit wrap dress so you can feel like you're still in your bathrobe, but *definitely* not look like it. It's one of those pieces that will make you look effortlessly chic, even when you've just rolled out of bed and haven't even had a caffeine boost yet.
6. A tie-waist minidress with lantern sleeves that's as cozy and comfy as it is stylish. The tie waist takes this number from casual to extra special, so you can wear it to work and for your festive holiday card photo shoot.
7. An adorable Peter Pan–collar long-sleeve skater dress to channel your inner Wednesday Addams (even when Halloween is 10 months away). You'll love the A-line skirt, fitted top, and contrasting collar, as well as the comfy, stretchy material it's made from.
8. A floral faux-wrap minidress that you can pull out for date night, holiday parties, or a winter wedding and instantly feel polished and put together. If you love a bold print and a ruffled hem, this one is for you.
9. A ribbed turtleneck bodycon you can easily dress up or down with the help of cute accessories and winter layers. It's super stretchy and comfortable and a great basic you'll have so much fun styling and wearing.
10. An oversized cable-knit sweater dress that's so warm and cozy, you'll actually change out of your sweats to wear it. The beautiful cable-knit detail gives this dress a high-end feel, and as one reviewer said, it's "slouchy, warm, cozy, and perfect for fall and winter!"
11. A boho patterned tiered ruffle dress because you need a piece that can transition from a long day at the office to eagerly awaited happy hour drinks in the evening. You'll want this stunning dress in multiple colors because you're gonna wanna wear it all the time.
12. A ruched velvet bodycon that's about to become your party dress of the season. If you've been in loungewear for way too long (and haven't we all), this soft and velvety dress will remind you of the good old days of dressing up and having places to go and people to see.
13. A flared checked midi dress with a high neck and bold pattern to wear with your favorite cool new belt. It's so good, you'll find yourself wearing this made-for-winter dress over and over, all season long.
14. A pencil dress with mesh bishop sleeves that you won't believe is under $40! The intricate flower details and beautiful materials give it a sophisticated look that's worth way more than its budget price tag.
15. An off-the-shoulder lace cocktail dress you'll want to wear for every party, event, and wedding this winter and beyond. Everybody needs a great LBD, but if you'd prefer a more vibrant color, fear not — this little number also comes in bold red, festive green, and classy navy.
16. A hooded sweatshirt dress that screams cozy comfort! It's made from sweatshirt material and has a hood and pockets; thanks, Amazon, we'll take one in every color.
17. A velvet maxi dress to wear to your twice-removed third cousin's wedding this winter. Sure, you've never actually met this supposed "cousin," but it'll give you an excuse to wear this gorgeous dress!
18. An oversized turtleneck sweater dress that's about to be the coziest thing you've ever worn. This sweater is ultra soft and roomy and, as if that wasn't enough, it has pockets, people. Add a pair of over-the-knee boots and you have a winning winter outfit.
19. An oversized minidress for when you don't want to venture out into the blustery cold but your nails could really use a fresh new mani...because priorities. It's the make-no-effort-but-still-look-cute dress you definitely need in your closet this season. And if you feel like mixing it up, it can also be worn with pants as a sweatshirt!
20. An elegant mesh-sleeve bodycon with beaded pearl detailing that will make you feel like the queen you are every time you wear it.
21. A lightweight sweatshirt tunic dress to throw on with tights and boots on repeat this winter. Get it in every color so people don't start getting suspicious whether you actually own any other clothing.
22. A ruched faux-wrap dress that's so good, you won't even mind the snow storm raging outside. Just grab a warm jacket, put on a cute pair of boots, and you're ready to brave the cold.
23. A loose-fit V-neck knit minidress to keep you warm but also looking cute when the temps dip below what's acceptable. If you hate parting with your summer dresses, this one might just convince you that winter ones are *just* as good.
24. A wrap-waist maxi dress for a winter basic that can be styled in so many ways. It's soft and stretchy, and guaranteed to be your new favorite dress as soon as you get it.
25. A cozy mock-wrap minidress with batwing sleeves that's just as comfy as your sweatsuit, but looks good enough that you can wear it for Sunday brunch without getting funny looks. Hello, weekly bottomless mimosas and French toast!
26. A cozy cable-knit turtleneck dress that's so cozy, it'll turn you into a winter person. Wear it with tights or leggings and a warm pair of boots for ultimate winter comfort.
27. A casual long-sleeve tie-waist dress that's cute, comfortable, and under $40! Oh, and it has pockets, for all the pocket lovers out there (that's *you*).
The reviews for this post have been edited for length and clarity.