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1. A workwear-style corduroy coverall even if your line of work involves typing on a laptop (whilst drinking a latte and talking to your dog in a baby voice) — not fixing up a car or unclogging a drain.
2. A pleated tie-neck blouse sure to become your go-to top because it's got volume, texture, and a breezy silhouette that won't constrict you after a particularly large brunch.
3. An edgy leather moto jacket if you yearn to be a person who just "throws something on" and goes but haven't quite nailed that down yet.
4. A pair of Converse Run Star Hikes with futuristic details like a two-tone exaggerated outsole, rounded heel, and chunky platform that'll lend you a few extra inches.
5. A long 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 tee combo.
6. A pair of Ugg Fluff Yeah slippers so you can pad around the house in Gigi Hadid fashion. She gave us the secrets to her spicy vodka pasta, so uh, yeah, we're gonna trust her opinion on slippers, too.
7. A black denim jacket with a cozy Sherpa collar that'll save you on particularly chilly falls days because despite your mom's sage advice, you did not grab a scarf on your way out the door.
8. A pair of faux-leather Spanx guaranteed to give you 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.
9. A mini leather bucket bag if you've been carrying around a ripped tote that's better suited for grocery store runs than any actual outings. This little beaut will make you feel so chic.
10. A wedding-appropriate silky wrap dress with deep-V neckline, an open back, and a calf- or thigh-baring slit (totally your choice if you wanna Angelina Jolie it up or not come photo time) 'cause chances are you have no less than three save-the-dates taped up on your fridge rn.
11. 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.
12. Or a pair of Dr. Martens Chelseas which 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.
13. A beige trench you can plop on over anything and immediately look like an incognito celeb — especially if you throw sunglasses and a mask (plz!) into the mix.
14. A simple but versatile mock-neck sweater with a half-zip design you can make use of when you forgot to match the shirt you're wearing underneath. Just zip that bad boy up and no one will be the wiser.
15. A quilted Free People jacket that'll allow you to roll through your day as if you never got out of bed. (AKA my absolute dream.)
16. A long 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.
17. A cowl-neck slip dress — woven from deliciously stretchy satin — for those looking to exude serious main character energy but with little added effort. Basically just put it on your body and go. 👍
18. A pair of essential fall booties with a chunky heel so comfortable and easy to walk in, you *won't* look like a newborn baby giraffe the first time you wear them out.
19. A heritage bomber from Alpha Industries — the very company that's been making hard-wearing apparel for the United States military since the '50s. Plus, who doesn't want to look like they stepped off the set of Top Gun?
20. A pair of Birkenstock's ultra-popular Arizona sandals lined with ~fall-friendly shearling~ for those who can't bear to put away their Birks even once temperatures start dropping.
21. A Reformation wool miniskirt if you're ready to roll through fall without ever pulling on a pair of jeans. Solved that for ya.
22. An AllSaints leather jacket with classic lapels and simple gunmetal finishings that make it a cinch to style. Like, seriously — throw it on over basically anything.
23. An oversized ~vegan~ leather blazer if the only thing your fall outfits are missing is some serious textural OOMPH.
24. A pair of dazzling star-embellished tights from D.bleu.dazzled — the brand behind some of Beyoncé, Lady Gaga, Lizzo, and Rihanna's go-to hosiery.
25. A thick, textured cardigan with voluminous sleeves and an easy fit you can pair with just about anything — even day-old sweats.
26. Or a chunky checkered cardigan you can throw on over jeans, wide-leg trousers, or a midi skirt for maximum pattern clashing. If you need further outfit inspo, a quick look through Harry Styles's fashion archive should also help.
27. A relaxed button-down dress — with ultra-comfy cotton construction — that can be worn two different ways sooo really...it's like spending $44 on two different dresses and not $88 on one, if ya think about it!
28. A pair of Frye harness boots which — when paired with your leather jacket — will bring your Justin Theroux look full circle.
29. A drapey Madewell blouse that French tucks like no other. Plus, the oversized fit means you can slip it on over your head without having to button it and then re-button it when you realize you were off by one.
30. A faux-leather jumper topped off with a ruffled collar that is very much giving me berries and cream but in a trendy, exactly what I'm looking for way.
31. A pair of Levi's Wedgie Fit jeans which will show off your best ~asset~ no matter what you throw on up top. Since they come in a bunch of classic washes, you might also want to pick up multiples. 😌
32. And a hand-knit mohair cardigan — the shade maple syrup, no less — with gorgeous oversized sleeves that are really the only thing people will be paying attention to. Accompanying skirt, shirt, overalls, who cares — those cozy cuffs are stealing the show!
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Unless otherwise specified, all sizes in this post are listed in women's.