Unless otherwise specified, all sizes in this post are listed in women's.
1. A teddy coat that's positively hibernation-ready but also sophisticated thanks to its tailored silhouette and large lapels. Your recipient can use it to dress up any outfit including the most basic (no haters) leggings and a tee.
2. A corduroy coverall (with a ~touch~ of spandex) that offers a one-and-done solution to dressing. No matching tops and bottoms here, folks!
3. A pair of criss-cross faux fur slippers with memory foam insoles that'll have them feel like they're walking on a literal cloud. Since they have a waterproof and slip-proof sole, they can also show them off while running errands.
4. A Slip silk sleep mask for blocking out early morning sun because while they love how their apartment is "drenched in natural light," it just doesn't jive with their sleep schedule.
5. A jersey sleep set with tulip detailing they'll certainly pull back curtain-style so they can admire their butt. That's something I'd regularly do, anyways 🤷♀️
6. A pair of faux-leather Spanx guaranteed to give your friend the confidence of Sandy (aka Olivia Newton-John) at the end of Grease. Unfortunately they don't come with a drive off into the sunset courtesy of the Greased Lightnin' car, but they are pretty dang comfortable.
7. A matching lounge set that we're calling 2020's version of the power suit. The two-piece fit promises to have them feeling like the most pulled-together version of themselves and it'll keep them cozy since it doesn't have any buttons, zippers, or constricting fabric.
8. A six-pack of velvet hair scrunchies because sometimes, a ponytail or messy bun is just easier and these will seriously level up the look. The '90s are alive in more than just Portland, that's for sure.
9. A Parachute Cloud Cotton robe that's amassed a cult following with its fluffy gauze construction and trendy color palette.
10. A popcorn-knit cardigan for days when they want to look pulled together but also feel like they're wrapped up in a throw blanket. And who wouldn't want that?
11. A pair of Outdoor Voices leggings with a pocket that can hide all of their secrets. JK, it's much better suited to phones, but who are we to tell them how to use their gift?
12. A classic blanket scarf that'll soon be the most versatile piece in your friend's closet. They can wear it as a regular ol' scarf, unfurl it into a shawl, fashion it into a travel pillow, or just use to trap their cat/dog in a burrito-style swaddle.
13. A drop-shoulder sweatsuit that's as close as one can get to wearing an adult onesie. Ofc with tapered legs, ribbed cuffs, and a cinched waist, regular onesies walked so this one could run.
14. A high rise thong from cult-favorite undie brand Parade because once you're a true adult, there are few things better than attractive, well-fitting undergarments. Sure, this pick won't be for everyone on your list, but some are sure to appreciate it.
15. A pair of goes-with-everything sneakers that — if your giftee is anything like me — may send them down the Everlane rabbit hole. (It's not a bad place to be, might I add.)
16. A body-con sweater dress that they can both sleep in and take IG-worthy photos in thanks to its sleek bat-wing sleeves, tie waist, and open back.
17. A set of stretchy, knotted headbands for days when they're all about dry shampoo. No matter the size of your friend's noggin, these boho bands will do just the trick.
18. A statement-making knit that celebrates Pride every day of the year and in one of the most comfortable fashions imaginable.
19. 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.
20. A wide-brim hat capable of blocking harmful UV rays and helping them on their journey to an Alexis Rose-approved closet.
21. A beanie and face mask duo because you care deeply about your friend's health in these oh-so-trying times! Other notable design elements: soft jersey lining and a plush pom-pom.
22. A faux fur purse that both has enough room for your giftee's phone, wallet, and keys, and will resurface treasured memories of their favorite pillow pet.
23. A pair of thigh-high boots with soft, stretchy suede and a chunky block heel that prevents blisters and knee and back pain. Finally, a chic and affordable boot you can confidently gift without an accompanying box of Band-Aids.
24. A pair of fanciful floral socks from woman-owned brand Sock Candy, because ~real adults~ know that they're a fun and practical gift! Sock haters can keep scrolling but also, feel free to forward me any and all pairs you receive this season.
25. 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.
26. A loose-fitting jumpsuit with a stylish keyhole back that beautifully blurs the line between pajamas and daytime wear.
27. A pair of wide-leg corduroy pants with plenty of give and even more flair. TBH I just snagged the green ones for myself, so friends and family — if you get me a second pair, go with black. Thx 😘.
28. 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.
29. A pair of fleece-lined leggings ready for winter's wrath. The much-loved bottoms have a wide waistband that stays in place and they're made from a moisture-wicking fabric that's certain to keep your friend nice and cozy.
30. A microfleece cardigan that's basically an office-appropriate robe because — reminder! — the year is 2020 and we could all stand to be more comfortable.
31. A crop top and jogger pajama set to deceive any onlookers (their roommates and quar pod friends, that is) into thinking they're holding things together better than most.
32. And, depending on what type of ~friend~ you're shopping for, an underwire-free bralette that can play peek-a-boo with the best of 'em but doesn't require constant readjusting.
Some reviews have been edited for length and/or clarity.