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1. A pair of short rain boots because we never really age out of wanting to splash through puddles, do we?
2. A pair of Hush Puppies ankle boots that look sleek and professional while still keeping you totally comfortable.
3. A pair of Bearpaw ankle boots perfect for that early fall chill. These boots feel like the Pumpkin Spice Latte of footwear in the best of ways.
4. Or a pair of high-rise cozy boots to keep those calves warm come wintertime.
5. A pair of fur-lined ankle boots if you aren't quite ready to commit to the Ugg-style look, but still want to be comfy and cozy all winter long.
6. A pair of lace-up combat boots that look like they're ready for just about anything.
7. A pair of high-heeled Chelsea boots I can picture myself totally living in through all four seasons.
8. A pair of comfy cowboy boots that are definitely Stagecoach ready.
9. A pair of Puma x Fenty sneaker boots for those who seek the comfort of a chunky sneaker combined with the elevated style of a boot.
10. A pair of patterned rain boots because a little rain shouldn't dampen your sense of style!
11. A pair of Dr. Martens Chelsea boots that are awakening the ~2014 Tumblr girl~ from deep inside of me. Siri, play "Girls" by the 1975.
12. Or a pair of Dr. Martens platform boots for an even ~edgier~ take on the lug-sole look. Would we call this grungecore? Somebody get me a flannel, STAT.
13. A pair of Sam Edelman penny riding boots that are ready to take you anywhere you'd like to go this autumn — from the grocery store to the equestrian center. Giddyap!
14. A pair of Hunter rain boots to channel the inimitable style icon ~Princess Diana~ all through the rainy season.
15. A pair of mid-calf platform boots that feel like the everyday shoe of your favorite stylish cartoon character as a kid. I am *so* here for it.
16. A pair of waterproof faux-fur-lined boots ready to carry you far in style this fall.
17. A pair of chunky combat wedge boots that are rave-ready but also comfy enough to carry you through your next grocery run. I ~personally~ have to be the edgiest person in the cereal aisle for some reason...
18. A pair of thigh-high suede stiletto boots because let's be honest — we've been thinking 'bout these boots ever since Ariana Grande's Sweetener era.
19. Or a pair of flat thigh-high stretchy boots if you're looking to channel that Ari energy in a slightly more low-key, cozy fashion.
20. Or try the best of both worlds with these chunky-heeled thigh-high suede boots, made for serving looks sans blisters or twisted ankles.
21. A pair of mid-calf square-toe boots destined to be your go-to fall shoe.
22. A pair of low-heeled Chelsea boots, which are somehow timeless AND trendy all in one stylish shoe.
23. A pair of block-heeled mid-calf booties that comes in multiple colors and patterns and are such a statement piece for the footwear section of your fall wardrobe.
24. A pair of retro go-go boots that may very well come in handy for Halloween, but will almost certainly become a staple in your rotation year-round. I personally always aim to channel Daphne Blake à la the live-action Scooby Doo film.
25. A pair of classy stiletto ankle booties that are most certainly made for strutting.
26. A pair of slouchy modern cowboy booties to add a western flair to your ~look~ without standing out too much in a city environment.
27. A pair of Timberland hiking boots that you hopefully won't feel like throwing over the edge of a mountain while hiking (see Wild to catch the reference).
Hopefully you found that pair of boots to help you strut your stuff all the way through fall and winter. Happy shopping!
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