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1. Tall, slouchy block heel boots that you can pair with any outfit, any day of the week. They'll add a sophisticated finishing touch to a basic dress or jeans outfit, and they have a side zipper, so you won't have to wrestle them on and off.
2. A chic white boot to add a pop of brightness and texture to your outfit, and prove anyone who says you can't wear white after Labor Day wrong.
3. A pair of platform booties with side goring that are casual yet chic — aka perfect for all your casual-yet-chic fall shenanigans.
4. A short rain boot to keep your feet dry on wet days, without totally sacrificing style. Plus, they're easier to walk around in than traditional galoshes.
5. A pair of Chelsea boots that will be your go-to shoe this season, because they're great for unpredictable weather. They're water-repellent, so you can wear them out and about, even when October has decided to drench you, without worrying about ruining them.
6. A pair of sparkly block-heel boots for those times you want to add some ✨ glitter ✨ to both your ensemble and mood. It'll be hard for anyone *not* to do a double-take when you walk by in these gems.
7. Suede boots with a sheepskin and wool blend lining that are an excellent dupe for a certain much pricier boot. These are perfect for running errands, hitting the pumpkin patch, or having brunch with friends.
8. Low-heeled boots because they have pointed toes and a sleek, simple profile. They're as effortless to put on as they are to pair with your favorite jeans and oversized sweater.
9. A pair of lug sole combat boots that are versatile enough to be dressed up or down, and modern enough to be a great choice anytime you want to add some edge to your outfit. Plus, they have a side zip, so you won't have to struggle with laces.
10. Waterproof heeled boots so cool looking, you'll want to wear them rain or shine. But when it does rain, you can go ahead and jump in a puddle or two.
11. A pair of pull-on ankle booties with an oh-so-soft faux suede finish and a block heel that will be a wardrobe essential. And since they're in a neutral shade, they'll match almost everything in your closet.
12. A fleece-lined clog boot to help you embrace the colder weather in style. They'll keep your toes snuggly and warm, and your shoe game on point. Plus, they have a convenient side zip!
13. A pair of Western ankle boots that are a little bit country and a lot of fun. The zipper on the side will make them a breeze to get on, so you don't have to worry about struggling and tugging them on (or, god forbid, using a shoehorn).
14. Low suede lace-ups because you would wear slippers 24/7 if you could, but these are the next best thing. They're cute enough to compliment a variety of outfits, and their wool blend lining will make your feet feel like they're being hugged all day.
15. A pair of quilted lace-up winter boots that are sherpa-lined, waterproof and lightweight. You can wear them strolling on the sidewalk or at an après-ski (even if you skipped the ski part).
16. A pair of stiletto ankle boots to add a spot of glam into your life. The cushioned insole helps these booties feel a bit more comfortable than your average stiletto.
17. A pair of Chelsea boots with lug soles and a stretchy fabric cuff that give them a cozy look and feel — it'll practically feel like a sweater for your ankles.
18. A pair of block heel Timberlands because they are timeless for a reason. They're classic, waterproof, and made for walking...or strolling.
19. Or a pair of Timberland boots with a 6-inch heel that are an elevated blend of timeless and trendy. Pair them with thick tights and a mini-skirt for some peak autumn style.
20. A pair of chunky combat boots because they are as comfortable as they are practical. Try them with leggings, a dress, and everything in between.
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