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Unless otherwise specified, all sizes in this post are listed in women's.
1. A fleece-lined hoodie because you can never have too many sweatshirts, especially ones that are as soft and relaxed as this one. It has a slight V-neck for style, and to make throwing it on over your head easier when you're running late to your morning Zoom calls.
2. A fuzzy shacket that's part shirt, part jacket, and all coziness. It has a slightly oversized fit that's ideal for layering, and two side pockets to keep your hands warm, too.
3. A quilted bomber jacket you're sure to reach for any time you head outside on chilly days. With a soft lining, collared front, and full-length zipper, it'll keep you warm without adding a ton of bulk.
4. A knit sweater for those days when you want something a little more stylish than the sweatshirt you've worn all week, but you still want to be comfortable. It's also versatile — you can roll up the sleeves or keep them down, tuck in the front, or leave it untucked, all for different looks.
5. A denim trucker jacket with an effortlessly oversized fit that is as classic now as it was in the '90s (except thankfully, now both you and your eyebrows have grown).
6. Tall, slouchy block-heel boots you can pair with any outfit, any day of the week. They'll add a sophisticated finishing touch to a basic dress or jeans outfit, and they have a side zipper, so you won't have to wrestle them on and off.
7. A pair of gloves made for anyone who would risk frozen fingers just to send a funny TikTok to their group chat. Now you don't have to — not only are these gloves made of a stretchy spandex material, but they also have touchscreen-friendly fingertips so you can text without interruption.
8. A mock turtleneck that goes beyond your basic sweater with extra details like a seam design and ribbed hem. The high neck eliminates the need to wear a scarf, and it pairs well with jeans or leggings.
9. A pair of platform booties with side goring that are casual yet chic — aka perfect for all your casual-yet-chic cold weather shenanigans.
10. An open-front cardigan so you can wrap yourself in warm coziness no matter what you decide to pair it with. A stained pajama top? Yes. The cutest sweater you've been dying to wear to brunch? Absolutely.
11. A blanket scarf to add that finishing touch to your seasonal OOTDs. It's also big enough to drape over your shoulders or legs in a pinch.
12. Comfy, high-rise sweatpants with trendy tapered legs, which makes them acceptable for either staying on the couch all day or spending the day out and about.
13. A puffer jacket with a hood to help you brave the elements. It has a sleek quilted design that allows you to zip it up all the way without turning into a giant marshmallow.
14. Low suede lace-ups because you would wear slippers 24/7 if you could, but these are the next best thing. They're cute enough to compliment a variety of outfits, and their wool blend lining will make your feet feel like they're being hugged all day.
15. Two pairs of marled socks made of a super soft fabric that will feel like fuzzy hugs for your feet. They'll make those cold morning floors just a little more bearable.
16. A pair of quilted lace-up winter boots that are sherpa-lined, waterproof, and lightweight. You can wear them strolling on the sidewalk or at an après-ski (even if you skipped the ski part).
17. Suede boots with a sheepskin and wool blend lining that are an excellent dupe for a certain much pricier boot (*cough* Uggs *cough*). These are perfect for running errands, holiday shopping, or having brunch with friends.
18. A ribbed beanie to keep your head warm and/or to provide a chic solution if you don't feel like doing your hair on any given day. You can wear it with the hem folded over or unfolded for a slouchy look.
19. A pair of Fair Isle socks that show your feet are ready for the wintry season. They're double-lined for warmth and tall enough to wear with your favorite boots so no snow or rain can touch your toes.
20. A pair of combat boots because it's officially boot season, and you need to have variety in your closet. These have laces, a side zipper for convenience, and enough of a heel to keep you walking tall.
21. A thick sweatshirt with a nice, quarter-zip opening so you don't get staticky hair every time you put it on or take it off. It also has a cute kangaroo pocket in the front so your fingers can stay nice and warm.
22. A hooded raincoat that pairs well with casual or dressier outfits. It doesn't look so rain jacket-y that you can't wear it on regular days, but it will help keep you protected when expected (or unexpected) showers hit.
23. A pair of fleece joggers made with a buttery fabric that will make you rethink the rest of the pants you own. They're as comfortable as pajamas but won't look like you just rolled out of bed if you wear them out.
24. A V-neck sweater just begging to be worn anytime the temperature dips below 50 degrees. It has a chunky, knit design you can wear all season long, and the ribbed cuffs complete the polished look.
25. A pair of fleece-lined clog boots to help you embrace the colder weather in style. They'll keep your toes snuggly and warm, and your shoe game on point.
26. A pair of wide-leg sweatpants that come in fun colors you can dress up or down. I'd be willing to bet you could even get away with wearing these out to dinner.
27. Soft slipper socks made with faux fur to keep your feet luxuriously cozy at home. And they have grippy soles so you don't have to worry about sliding around next time you run to the door for your Uber Eats.
The reviews for this post have been edited for length and clarity.