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Unless otherwise specified, all sizes in this post are listed in women's.
1. An oversize sweater vest to pair with a turtleneck or button-up for a classic Anglophile look — or switch it up for an edgy look and layer this over your favorite oversize black band tee.
2. A quilted bomber so you can keep warm going to and from parties without shorting your typical skater-chic style.
3. A pair of high-waisted straight jeans will go with practically anything you have in your closet, from cozy tees to crisp button-ups. This cut is great for emulating the early 2000s since it has a slight flare!
4. A pair of faux-leather leggings, because although the look of leather pants is beautiful, the feel of actual leather pants is...restrictive. Opt for this pair that'll look chic but feel like your favorite pair of yoga pants.
5. An oversize teddy bear coat that's the key to dressing up any outfit, even a standard T-shirt and legging get-up you'd wear to your 8 a.m. lecture. (Bonus: Having class that early in the morning is grim, but at least this fuzzy, blanket-like coat can offer some cozy reprieve.)
Some reviewers recommend sizing up for a slouchy fit and more room to layer.
Promising review: "OBSESSED!!! Exactly like a coat from Urban Outfitters except at a fraction of the cost. It's super comfy and warm! Love, love, love it! It feels expensive and is super cute. You don't have to spend so much money on trendy items — it's so not worth it when you can find cute dupes." —Vanessa
Get it from Amazon for $41.99+ (available in sizes S–3XL and in 35 styles).
6. A plaid miniskirt, because what is dressing for the winter if it doesn't include at least one piece of all-plaid clothing?!
7. A cashmere mock-neck sweater so that you can rock the look of a turtleneck without overheating in a warm city apartment!
8. A brushed coat with a belt, because the secret to looking cute in the dead of winter is dressing in layers! Consider sizing up with this coat (or any coat, really) so that you can fit thermal layers and sweaters underneath for a city-chic vibe that ACTUALLY keeps you warm.
9. A floor-length velvet dress that is so fitting for the Barbiecore trend that's all over TikTok and the red carpet. This ups the ante on a warm fabric like velvet with a fun color and trending wrap silhouette.
10. A pair of plaid leggings, because these leggings are so cozy you'll forget that you're even dressed up to the nines.
11. A boxy button-up so that you can stay Zoom-ready while dipping your toes into the coastal Grandma trend. This top is perfect for layering under crew neck sweaters or wearing tucked into your favorite high-rise trousers.
12. A 100% leather cropped suede moto jacket, since your jackets have the right to be as cool as you are, darn it! This jacket plus a silk slip dress is *chef's kiss* perfect for any casual cocktail event you've got on your docket.
13. A velvet bodysuit with a striped design that amps the va-va-voom potential of a classic striped top! This top plus a flared miniskirt is a great outfit for your next holiday party.
14. A jersey pajama set that you'll need to look cute and stay cozy during wine and cheese nights with your best friends.
15. A corduroy button-up, because corduroy is one of the few fabrics that screams, "Yes, the temperature is dropping, but I still want to look amazing!" Wear this little number buttoned up to keep you warm throughout the day, or use it as a layering piece during a Sunday brunch with friends.
16. A longline plaid jacket that adds a vintage professor-chic edge to your fit. If your fall vibe is 'I look like I study romantic poetry at Cambridge,' then this jacket is a must-have.
17. A striped knit sweater, because you'll need a cozy sweater to wear during your WFH days, so why not make it a cute one?
18. A SKIMS ribbed pajama set that feels like butter on the skin and looks like what one would wear when waking up in a fancy hotel. I love this set because it wraps me up in coziness as I snooze away, yet has a structured lapel that makes me feel like I'm wearing "real" clothes if I end up working in my PJs.
19. A classic turtleneck, since no winter wardrobe is complete without a bit of turtleneck action! Pair this with a plaid skirt for an elevated back-to-school look.
20. A pair of low-rise corduroy cargo pants so that you can rock the low-rise pant trend that's surfacing on TikTok while staying warm with the classic winter fabric.
21. A pair of sherpa clog slippers, since clogs are officially back! These shoes have a cork sole (much like your beloved Birks) and are perfect to use as slippers at home, during early morning walks, or even while running errands around town.
22. A henley top, because this base layer is what will keep you warm during those late nights spent around the fireplace. Consider getting a few — after all, henley tops also work great as loungewear around the house.
23. A pair of palazzo pants if you're in a part of the country that doesn't get too cold, but long pants are still a necessity. These allow the breeze to flow, while still making you look put-together if you're heading to the office.
24. A pair of buttery soft leggings because the bottom half of your Zoom outfits deserve an upgrade too! If you don't find yourself in front of a webcam much these days, this pair is also great to wear during your daily runs (reviewers say they're super moisture-wicking!).
25. A scout jacket if you're someone who is currently living in a place that doesn't reach *extremely* frigid temps as the year ends. With a jacket this fashionable (and light), you'll actually listen to your elders who tell you that you NEED a coat to leave the house in December.
26. A turtleneck bodycon dress so that wherever you go, you'll be arriving in style. This low-key, go-with-everything dress is perfect for days when you want to wear every single winter accessory under the sun.
28. A reindeer skull sweater so you can rock an on-theme top for the upcoming holiday sweater party while letting your edgy style peek through.
29. A chunky cableknit cardigan that you can wear around the house to cozy up, or with a belt and dress to spice up your hot cocoa-making fit.
30. A set of fishnet stockings to pair with your favorite skirt and over-the-knee boot ensemble. Plus, these come in a variety of quintessential winter patterns, meaning that you'll have SO many opportunities to add a cool-weather flair to your style.
31. And a wrap top that is in line with your newfound style, the ~ballet core~ aesthetic, while keeping you warm under the blaring AC at work!
The reviews for this post have been edited for length and clarity.