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1. A rugged sweater to quickly add some style and warmth to a white button down or chambray shirt.
2. A set of reusable face masks in low-key colors and patterns because you're ready to experiment with fashion masks but aren't really sure where to start.
3. A Levi's western shirt so versatile, I'm yeehawing just thinking about all the different ways to wear it.
4. A corduroy baseball cap that might be the only accessory you need this fall. It goes with everything and makes bad hair days a thing of the past.
5. A premium-weight long-sleeve crew from Everlane with raglan sleeves that make this base layer equally cool and collected all on its own.
6. A Carhartt pocket T-shirt to round out the workwear-inspired wardrobe you've been curating over the past few months.
7. Dress socks in spunky colors and patterns that pair just as well with suits as they do sweatpants and sandals.
8. A felted chore coat from Buck Mason in a soft, boiled-wool fabric that'll make the perfect top layer for all your WFH fits.
9. A pair of Nice Laundry pocket lounge shorts that, and I am not exaggerating, you will never want to take off. Period.
10. A cardigan sweater with a shawl lapel and warm, textured knit you can wear literally anywhere (think sweatpants on the couch, or with jeans and a flannel when you're apple-picking with your in-laws).
11. A pair of black sneakers that do it all: they're simple, stylish and sophisticated.
12. A pair of cutoff cargo pants that offer up a relaxed fit and cropped ankle, hitting at just the right length to show off your new high-tops.
13. Darn Tough boot socks to keep your feet warm and dry without the bulkiness and irritation of standard wool socks.
14. A timeless turtleneck sweater that'll always be appropriate whenever you can't decide what to wear.
15. A Ben Davis beanie because keeping your head and ears warm isn't that deep — this one's soft, affordable, and comes in a handful of cool colors.
16. A Levi's sherpa-lined trucker jacket for a cold-weather take on the classic denim jacket.
17. A tailored-fit sportcoat because fall is a great time to update the "dressier" pieces hanging in your closet.
18. A Noah rugby shirt in a heavyweight jersey knit that's a bit of a splurge but is sure to win the praise of all your buddies.
19. A lightweight, laid-back scarf that'll make you look like you put a lot of thought into your outfits without putting in any at all.
20. A crewneck sweatshirt for an effortless staple you can easily accessorize to make it your own.
21. A pair of high-top Vans to instantly add a pop of color to all your cool-weather looks.
22. A full-zip hoodie made in a micro-ribbed cotton twill that's sure to set it apart from those ratty sweatshirts currently shoved in your dresser drawers.
23. An Alex Mill garment-dyed work jacket to layer over button downs, hoodies, and graphic tees.
24. A pair of Madewell jeans that've been garment-dyed to spice up your current denim rotation without having to sacrifice fit or comfort.
25. A windbreaker from The North Face to make harsh weather as bearable as possible.
26. A pair of Blundstone boots you'll want to wear year-round because of how easy they are to slide on and off while still being incredibly weatherpoof.
27. A Carhartt Detroit jacket featuring a blanket lining and a corduroy-trimmed collar equally suitable for the garage as it is for the street.
28. A double-brushed flannel that'll have you looking as cool and crisp as the days ahead.
29. A lightweight bomber jacket to polish off everything from a button down and chinos to sweatpants and sneakers.
30. A twill pocket shirt for a modern, more casual take on the quintessential white button-down.
31. A Patagonia fleece zip-up that's sure to be the wind-blocking, heat-trapping, show-stopping number you've been looking for.
32. Champion jersey sweatpants, a lighter-weight alternative to their classic closed-bottom sweats that are frankly just a tad too toasty to lounge in.
33. Or, a splurge-worthy sleep pant from Marine Layer, made from the same fabric as their bestselling boxers and briefs.
34. And a pair of memory-foam slippers to pair with your new lounge pants — they're cozy enough to wear around the house, but durable enough to withstand the elements when you run out to grab the mail or walk the dog.
35. A pair of pinstripe sweatpants that totally don't look like sweatpants, so you can feel dressed up with actually being dressed up.
36. A collapsible tote because you suddenly have a lot more things to carry with you: extra face masks, hand sanitizer, head phones, mints, lip balm, gloves...
37. A breathable performance henley from Bonobos that, with its luxurious cotton blend and moisture-wicking fabric, you'll definitely want in every color.
38. A pair of pleated corduroys with a relaxed fit and cropped inseam guaranteed to be the coolest pants you've had in a while.
39. A full-zip fleece vest you can wear as a top layer when it's just a little chilly outside, or as a base layer when the time comes to truly bundle up.
40. Dickies work pants, the classic pair-with-anything trousers that are wrinkle and stain resistant — need I say more?
41. A pair of Clark's Wallabees made with 100% leather and a crepe soul that work together to form one beautiful, highly-durable, ultra-comfortable pair of boots you'll never want to take off.
42. A long-sleeve waffle knit with elastic cuffs and a straight hem that make it perfect for layering under a vest or flannel.
43. A nylon rain jacket because there are definitely autumn days when it rains or snows but it's not quite cold enough yet to sport your winter parka.
