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Unless otherwise specified, all sizes in this post are listed in women's.
1. Classic Bean boots for all types of messy weather *and* for that New England chic vibe. Rain, snow, mud, and crunchy leaf approved!
2. A Sorel wedge bootie that'll give you all the style of a heel with all the function of a boot, making it the ideal *leaf-crushing* shoe.
3. Madewell loafers so chic, you'll be able to wear them with any outfit and have your entire look immediately look 10x better. "Dang, you look so cute." —The leaves as you step on them
4. Slip-on loafers you can style with just about any outfit imaginable. Plus, the fact that they're slip-on makes them so easy to just, well, slip right on and head on to your next leafy trail.
5. Slip-on mules that you'll probably end up wearing for all of fall (trust me). They're comfy *and* stylish. Name a better duo. I'll wait.
6. Adidas Grand Court sneakers because Gen Z brought these '90s bad boys back and honestly I'm not mad about it. "Am I cool yet?" —Me, to that one maple leaf I took a photo of to post on my Instagram feed
7. A pair of cheeky boots that are basically made to be worn by one of the Sanderson sisters and will have you yelling "Boooook!" out your window the second you lace them on.
8. Colombia hiking boots that are waterproof, lightweight, *and* have advanced traction rubber soles to handle any kind of terrain you put in their path. These are basically perfect for those uphill hikes where the leaves are making it extra hard to climb.
9. A pair of clogs that you may think are clunky and weird, but I promise you, they'll look absolutely adorable on you!
10. A pair of vegan oxfords you could pair beautifully with slacks, a white button-down top, and an oversized blazer for the "college professor in the middle of fall" look.
11. A pair of stylish red boots because everyone needs to have that *one* pair of shoes that they're basically known for. These will be yours while you strut down a trail full of leaves.
12. A pair of sleek Chelsea boots that'll quickly become your go-to shoe for every single outing *and* for many years. Think about all the leaves these baddies can step on throughout their life.
13. Or a Chelsea boot that'll save you a *wee* bit of money, because they're not just a wardrobe staple, but a wardrobe *must-have*.
14. Or! Extra-budget-friendly Chelsea boots because these boots are, quite literally, made for walking on leaves, and everyone deserves to rock them. They've got a thick heel, which provides extra support so you can walk for miles and still be comfortable (and stylish!).
15. Betsey Johnson booties that are honestly giving me some serious Emily in Paris vibes and I'm living for it.
16. Platform Mary Jane heels for when your aesthetic is "I want to look cute while I walk on leaves but also make it edgy."
17. Western-style boots that'll have you "yeehaw-ing" all over your town's fall leaves feeling like Miley Cyrus circa 2010.
18. Hunter boots that, OK, *are* teeechnically rain boots, but hey it rains in the fall and leaves get slippery to walk on! You'll be safe and stylish. I'm just thinking of you.
19. Doc Martens combat boots so you can finally jump on this bandwagon that is definitely here to stay. They're wicked reliable, so you can wear them through rain, sleet, and even snow! Oh, and also leaves. Don't forget the leaves. Ever.
20. Or Sam Edelman combat boots, for when you like the Doc Marten look, but the neutral colors of these just suck you right in.
21. Thigh-high boots that'll have the leaves going "Are those the—" "The Vogue boots from a small business? Ya. They are." Then you flip your hair and the leaves ogle your style as you step on their faces.
22. Jeffrey Campbell booties so you can get the support of a regular bootie but with utter ~style~ thanks to the ultra chic cutout and metallic accents.
23. Simple pointed ballet flats to step it up from your old ballet flats that look like something your niece would wear. The pointed toe will *always* make your flats look better than a rounded toe, and you can fight me on that (please don't, I am soft).
24. Square-toe boots guaranteed to become one of your new favorite pair of boots to crush leaves with. They're sleek, chic, and give juuust enough height that you feel tall and mighty without compromising support.
25. Houndstooth booties so you can look put together and ~oh so chic~ for work. Bonus points if you can collect 10 leaves onto your heels before you make it to the office.
26. Sam Edelman loafers that are kind of giving me ~Elton John vibes~ and I'm living for that aesthetic, honestly. There are 41 (!!!) colors to choose from so you'll always be able to match your loafers to your outfit. A dream come true.
27. Heeled riding boots that are perfect for anyone who doesn't want to let go of the riding boot trend from a few years ago —it's me. I will die on this hill I climbed while wearing these boots and simultaneously stomping on crunchy leaves. Hmph.
28. Chunky white sneakers because 1) they're so ridiculously comfy and 2) they're unbelievable cute. Trust me, you don't need boots to frolic in piles of leaves. Pair these bad boys with mom jeans, a slouchy turtleneck, and your favorite bag. *chef's kiss* Perfect.
29. And finally, Skechers walking shoes that are quite literally made for walking. And you know what? That's just what they'll do. All over those crunchy leaves.
The leaves, after you've walked all over them:
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