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Unless otherwise specified, all sizes in this post are listed in women's.
1. A pair of Chelsea ankle boots with a lug-sole design and chunky block heel that'll be your go-to autumn/winter shoe. They're very comfy and will ~elevate~ any cozy sweater and jeans outfit.
2. Platform sneakers you'll love for outdoor adventures and grocery store trips. They'll dress up loungewear or comfy jeans, and give you great cushioning.
3. Rain boots that'll actually keep your feet dry, prevent you from slipping on muddy areas, and double as a chic footwear option on drizzly autumn and winter days.
4. Chunky Mary Janes to pair with fun ankle or ruffle socks when you want a break from tights. These '90s-inspired beauties will complement lots of fall clothes, including flare jeans and midi skirts.
5. Adjustable mid-calf booties because they'll keep your feet warm without weighing them down. If you need a fall/winter boot that's stylish, waterproof, and not too heavy, these cozy gems will be great when the weather gets colder.
6. A pair of handwoven, slip-on shoes, so you don't have to sacrifice comfort or style when it's too cold for sandals. They have cushioned insoles and breathable material that'll keep your feet feeling sweet all season long.
7. Suede boots because they'll match everything in your closet (even dresses you still want to wear during the fall and winter) and hit your knees at the right spot.
8. Loafer flats that'll feel so good on your feet, you'll forget you're actually wearing cute shoes. They won't feel too tight on your toes or rub against your heels whenever you're on the go.
9. Chelsea boots because you need a shoe that'll go with everything in your closet and last during the colder months. They have amazing traction (buh-bye, sliding on leaves and snow), a durable exterior, plus a pull-on design that makes them easy to take on and off.
10. Vegan oxfords perfect for the office or working from home. Each pair is handcrafted in Mexico and comes in a neutral shade that'll look lovely with long-sleeve blouses, blazers, and suit pants.
11. Chunky Filas because you can't go wrong with a classic sneaker that'll ~step up~ basically any loungewear ensemble. Bike shorts? Check. Leggings? Check. All you need is a cozy sweatshirt and you'll be good to go.
12. Square-toe boots to replace your summer wedges and heeled sandals. If you want a little more height without exposing your toes to the cold, these shoes will get the job done.
13. Slip-on sneakers ensuring comfort if you're on your feet all day. They have amazing cushioning, a lace-free design, *and* come in a bunch of colors for your fall/winter wardrobe.
14. Lace-up combat boots that'll add a tiny bit of edge to your outfit and get you excited to wear denim jumpsuits and cozy leggings again when fall is in full swing.
15. Or platform creepers so you can take your feet to new heights and pair your fishnet tights *or* skinny jeans with a cool combat boot alternative.
16. Comfy pumps you'll want to wear for formal fall and winter things: They have a low heel and cover your toes, so you won't have to change shoes frequently if it's cooler outside.
17. Everyday boots for commuting, lounging, and everything in between. With cushy insoles, a waterproof upper, and a soft lining, you'll be ~walking on sunshine~ from fall to winter.
18. Colorful sneakers to slip into if you're bored of basic shoes and don't want to sacrifice comfort. These will look so cool on you whenever you're out and about.
19. A pair of waterproof Columbia hiking boots for trail walks. With waterproof construction, breathable linings, and a durable bottom, you won't have to worry about falling on your butt, sliding around in muddy areas, or having soaked feet.
20. Wide-calf riding boots to keep you warm *and* complete your fall or winter uniform that may include cozy leggings or tights with a skirt. They have faux fur lining (bye-bye cold feet) and a stylish quilted design.
21. Mary Jane flats so timeless, gorgeous, and splurge-worthy for your closet. If you want to ~dress to the nines~ for a special occasion, these gems will work with dresses, skirts, and sleek pants.
22. Ugg shearling-lined boots that'll be like wearing your favorite pair of cozy slippers all the time: Your feet will be nice and toasty and you won't slip, thanks to a durable outsole with great traction.
23. Ankle booties so you can look cute and walk comfortably through an apple orchard, pumpkin patch, or farmers market.
24. Faux shearling slippers that'll keep your feet toasty whenever it's a little chilly indoors. You can wear them alone or with your fave pair of socks for all the cozy feels.
25. A pair of luxe-looking mules you'll wear again and again, because they're so comfy, fashionable, and make a great dupe for expensive styles you've been spotting on Instagram.
26. Waterproof duck boots that'll be a classic footwear option if you're dreaming of walking through crunchy leaf piles all season long. Your feet will stay comfy and dry, even if it's a little damp and rainy outside.
27. Chunky over-the-knee lace-up boots to wear if you want an easy, no-fuss autumn or winter OOTD. Add in your favorite chunky sweater and pair of faux-leather leggings and you'll be all set.
28. A pair of huarache sandals perfect for those days when you luck out with autumn or winter weather and it's not too hot or too cold: they're made with a comfy leather material and go with so many wardrobe staples (denim, dresses, skirts, and more).
29. Platform oxfords just begging to be part of your fall/winter shoe lineup. Their gorgeous color will literally go with everything in your closet — blazers, baby blue denim, mini skirts, you name it, and score you major compliments.
30. Kamik waterproof boots for chilly fall and winter days ahead: walk through mud, rain, *and* snow without drenching your feet thanks to a faux-fur collar, waterproof material, bungee laces, and a very grippy sole.
31. A pair of athletic sneakers that are lace-free and feel like a soft cocoon around your tootsies. Just ~slip~ them on whenever you're taking a walk around the neighborhood or hitting up the treadmill at home.
32. Platform boots so chic, you'll probably tell your booties, "sorry, we're taking a short break" as the weather gets colder. An added bonus? You'll have footwear that elevates any sweater and mini skirt look.
33. Steve Madden ankle boots with pretty gem detailing and a chunky silhouette for autumn and beyond. Fishnet tights or thigh-high stockings will top off these trendy shoes that aren't your basic pair of footwear.
34. Low-wedges to slip into if you're really, really getting tired of boots and other closed-toe shoes. They're affordable *and* help dress up your favorite pair of jeans or pants.
Reviews have been edited for length and/or clarity.
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