39 Winter Wardrobe Staples Sure To Please Anyone Who Prioritizes Style *And* Comfort
'Tis the season for Sherpa, faux fur, and fleece 😍
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Unless otherwise specified, all sizes in this post are listed in women's.
1. An oversized wool coat that envelopes you like an absolute dream with its drop shoulders, statement lapel collar, and massive pockets. Like really — you could fit a Chipotle burrito in there.
2. A pair of fleece-lined leggings so incredibly soft and warm, you just won't believe it. If you've been eyeing a pair from Spanx but don't have $100 to shell out, they're a great dupe!
3. A pair of fuzzy mittens because if you're anything like me, you refuse to stop getting iced coffee even when it's only 10 degrees out. Protect your skin mitts with these faux-fur mitts and you're good, bb!
4. A corduroy button-down that'll help you nail that "oh, this? I just threw it on" look that all of your favorite stars have down. (I'm looking at you, Dakota Johnson.)
5. A pair of Ugg Ultra Mini Ankle Boots so you can pad around in peak "Yes, I follow TikTok trends even though I'm 30" fashion.
6. A simple mock-neck belted sweater dress because sometimes, just having to change out of PJs and then pick out undergarments is already more than I can handle.
7. A teddy coat that's positively hibernation ready but also sophisticated thanks to its tailored silhouette and large lapels. You can use it to dress up any outfit including the most basic (no haters) leggings and a tee.
8. A trusty pair of opaque tights you can slip on under skirts and dresses (heck — even distressed denim) on days when the windchill is notttttt playing.
9. A one-and-done black jumpsuit if the ***one thing*** you miss about private school or your first fast-food job was the convenience of throwing on your uniform and getting out the door.
10. An oversized plaid shacket that my family back in New Hampshire would really get a kick out of cause they've been wearing them for function, not fashion (and since before I was born), but here we are!
11. Or a longer plaid shacket because it's FINALLY the season for lots of layers and — in case you haven't been on social media in a hot second — this look is in, bb.
12. A slouchy buckle sweater if your go-to winter fashion is oversized knits but you're looking for something with a twist.
13. A five-pack of knit socks that'll come in handy whether you're lounging around at home with cold tootsies or slipping on booties to run some errands. (AKA walk around Target and see what calls your name.)
14. A pair of ~comfort stretch~ flared high-rise jeans because, as we all know, fashion is cyclical and wide-leg denim is back for its seventh (or so) moment in the sun.
15. A 100% cashmere sleeveless turtleneck that'll not only come in clutch when its chilly, but also be able to effortlessly transition season to season. It's the garment that just keeps on giving.
16. A pair of Birkenstock's ultra-popular Arizona sandals lined with ~winter-friendly shearling~ for those who can't bear to put away their Birks even once snow starts falling.
17. A ponytail-/messy-bun-friendly beanie ready for winter #OOTD selfies and startlingly cold temps. A hole at the top of the hat allows them to pull their hair through with ease and an elastic keeps their do in place.
18. A pair of slouchy faux-leather pants with a high-waisted design and ankle-baring cut so you can up the ante with your coolest footwear, too.
19. A cozy sweater dress that, as you can see below, looks fan-freaking-tastic with thigh-high boots but can also be belted or worn with tights. (Unpopular opinion: I LOVE wearing tights and would happily do so year-round if it was cool enough out.)
20. An exceptionally soft cashmere sweater you can turn to on days when you feel like putting zero effort into your outfit but you still want to look perfectly pulled together.
21. A 4-in-1 Universal Standard puffer with a removable hood and bottom so you can skate through late fall and the freezing winter temps without the need for more than one coat.
22. An oversized waffle-knit sweater that can be styled three different ways: one shoulder, double off-the-shoulder, or as a classic V-neck. Reviewers all agree it's a perfect dupe for many of Free People's most popular thermals.
23. A pair of Dr. Martens that can not only keep up with daily wear for more than a decade (I attest to this!) but also add some serious edge to your silk midi skirt + sweater combo.
24. Or a pair of Aussie-adored, beat-'em-into-the-ground Blundstones that'll still bounce back after countless romps through mud puddles, snowbanks, and even cow manure.
25. A cropped faux-shearling jacket to emulate your favorite faux-fur throw. If you can't be on your couch wrapped up in its embrace all night long, this is at least the next best thing.
26. A three-piece hat, glove, and scarf set if you love a matchy-matchy look but lost last season's go-to set.
27. A chunky oversized sweater guaranteed to keep you snug as a bug in a rug even though you're a human who exists exclusively in Spanx faux-leather leggings.
28. An oversized plaid peacoat you can throw on over anything and immediately look like an incognito celeb — especially if you throw sunglasses and a beanie into the mix.
29. A crisscross backless sweater that's all business in the front but party in the back because despite the fact that you only wear neutrals, you're never one to be boring.
30. An oversized ~vegan~-leather blazer if the only thing your fall outfits are missing is some serious textural OOMPH.
31. A rib-knit skirt you can wear at your natural waist or hike up for a shorter silhouette. It's like getting two skirts in one!
32. A pair of Levi's pull-on skinny jeans if you're someone who doesn't like leaving the house in loungewear but wants to *feel* like they're wearing loungewear nonetheless.
Promising review: "OK, I'm not going to lie. I was skeptical about these pants. I hate buying clothes online without trying them on first, but the reviews here said that they runs true to size, so I trusted them. I am SO GLAD that I did. These pants are everything I ever wanted. Make my butt look cute? Check. No nasty zipper to dig into my gut? Check. Perfect length for any season? Check. I can wear these with a cute blouse as a teacher, and still look professional, while still being comfortable. I feel comfortable wearing these basically any time, and I think that if you're lacking a pair of them and thinking about it, you should go get a pair. They're AMAZING." —AlySedai
Get them from Amazon for $18.51+ (available in women's sizes 2–28, in three lengths, and eight washes).