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Unless otherwise specified, all sizes in this post are listed in women's.
1. A trendy teddy coat in a neutral tone that'll help you ease into the style without feeling like you're committing to a fad.
2. A pair of high-waisted leggings that, yes *are* opaque, and you'll want to buy in each and every color and then wear all winter whether you're working or werking out.
3. A cowl-neck tunic dress *so* incredibly chic and low-key that people may assume you're a heroine of a Nancy Meyers movie. Spoiler: You ARE.
4. A metallic pleated skirt that'll look ANYTHING but basic YET will match so many things that it'll earn its keep in that category. (And this story.)
5. Leather smoking shoes for a reliable classic that'll still be in style years from now — just be sure to get 'em resoled before they get too bad!
6. A trusty leather tote to contain all the everyday items you require on the reg.
7. Or a ~reversible~ faux-leather tote that'll give you a little more flexibility when you realize your outfit would look so much better with a black bag. Dump the contents, flip it inside out, rake everything back in, and be on your merry way!
8. Hunter rain boots for keeping your feet dry while frolicking through fields of wild flowers or dodging suspiciously dark puddles on city streets. Is that a coffee puddle or is it....
9. Or some sneaker-style rain boots you'll come to rely on for those days when it's a 30% chance of rain and you 100% don't want to ruin your good suede ankle boots OR sweat it out through wellies. And if it doesn't end up raining, it's NBD.
10. Knit jeggings so you can get away with wearing not-pants while wearing a socially acceptable semblance of pants.
11. A turtleneck sweater that'll look you paid so much more money on, welcome to scamming!
12. A colorful wrap dress — in straight and plus sizes — for something that's office dress code–approps without being a total snore.
13. Ankle booties in a range of colors (not just animal print!) that'll look fantastic with all kinds of ensembles. Dresses and tights, shorts, jeans, nothing at all?! You decide!
14. A water-resistant packable puffer coat for everyday wear or that bucket-list trip to Iceland where you plan to *just* carry on.
15. Or a metallic puffer that'll brighten up your winter looks while still matching most everything. Bye black puffer!
16. A sleek cross-body bag in a chic silhouette to help you feel a bit dressy, even if you're wearing that sweatshirt outdoors you've been rocking all week as you WFH from your couch.
17. A rubberized rain coat for gloomy mornings when you can't dramatically drape yourself across a couch indoors. Sigh.
18. Dr. Martens that'll be a tough go-to for days when the sun is shining or it's beyond gray. Plus, they come in a tons of colors in case your version of basic is anything but black.
19. An original Levi's trucker jacket with a multitude of styling possibilities that'll keep it in constant rotation.
20. Pointed-toe flats with just enough flash (and a bunch of colors) to add a little fancy flair to an outfit you picked up off your bedroom floor.
21. A striped tee for elevating a pair of old jeans without sacrificing your comfort level. Also, how cute will this look at casual holiday functions with a cardi thrown on top? Almost too cute.
22. A plaid scarf you can nuzzle into allll winter long. And into the spring when it's still a tad chilly.
23. White Superga sneakers as a fashion girl step up from your Keds (sorry Keds).
24. A seamless turtleneck bodysuit as a base for a multitude of cute outfits. Your pants and skirts will wonder why it took you so long to make an intro.
25. A Buffalo plaid flannel shirt for a winter classic that'll be the next best thing to wearing your flannel PJs out in public — though I'd argue that's acceptable behavior.
26. Versatile ballet flats you'll throw on in a million different ways on the days when you can't or won't with heels.
27. A solid dress with pockets for so much wardrobe versatility, you'll wonder why you didn't buy it in every color (there are 19, BTW!) from the start.
28. A cozy eco fleece sweatshirt ready to replace that old stained one. Or at least you can wear this one out in public and the stained one *just* in the house, k?
29. And a sweatshirt dress for the times you'd prefer to leave the house in a sweatshirt and no pants. Well now you can!
30. Chunky Chelsea boots as a boost for really most anything in your closet.
31. A tie-front shirt that'll make passersby think you have a tailor at your beck and call.
32. A Carhartt beanie that'll look good on anyone and everyone. And it comes in so many colors, everyone in the fam can have their own. Maybe even two!
33. Tortoiseshell sunnies you can get with single-vision or reader lenses so you'll always have these at the ready for strolls or leisure drives.
34. A ribbed polo that'll magically go with all the bottoms in your closet. Yes, I'm a magician.
35. A lightweight tunic that'll easily go with whatever pair of leggings are clean atm. (It's truly a struggle.)
36. And some See By Chloé knee-high boots to finish off your sweater-leggings lewk.
37. A simple cardi you can throw on to fight your frigid surroundings but keep you looking polished.
38. Stud earrings as a finishing touch before you head out the door.
39. A faux-leather motorcycle jacket to throw on over nearly anything, even when you're running to the gym!
40. Slip-on sneakers in a quilted style that'll make every well-cushioned step look a bit fancier.
41. A lacy LBD (that comes in other colors!) to help you look like a slightly better dressed version of yourself.
42. A mock turtleneck in a range of colors that'll be perfect for layering under your fave summer dresses or flying solo.
43. And some stainless-steel hoops to give any outfit a boost.
Reviews have been edited for length and/or clarity.