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1. A pair of chunky ankle boots with a whopping 8,000+ reviews and a 4.5 star rating, so you can feel 100% confident in your purchase. The combination of a 3.5" heel, a pull-on silhouette, and a classic, go-with-anything design.
2. A pair of Lucky Brand ankle boots with stylish, side zipper accents that are so cute (and versatile), you won’t be able to stop wearing them. With 40 colors to choose from, you are guaranteed to find one that will fit seamlessly into your wardrobe.
3. A pair of rubber knee-high rain boots so you can jump into every puddle you see. They are lightweight, weather-resistant, and fortified with anti-slip grooves — and they aren't agonizing to wear and won't cut into your feet, unlike many other rain boots.
4. A pair of durable, over-the-knee boots that will look great with everything, from skirts and dresses to jeans and leggings. Thanks to the fact they are made with ultra stretchy fabric, you won’t feel constricted at all, despite their length.
5. A pair of hiking boots because they're designed to withstand the elements, so you will be prepared for just about anything. They are anti-skid, wear-resistant, water-resistant, AND as cute as can be — what more could you want!?
6. A pair of Dr. Martens Chelsea boots that will likely last you years, and years, and even more years. These boots, which come in seven different colors, may be a little rigid on your first wear, but trust me, after being broken in, you will feel like you’re walking on Cloud 9.
7. A pair of Western-inspired ankle boots so you can channel your inner cowgirl all autumn long. Not only are these my favorite shoes I own, but I adored how they were comfortable to wear straight out of the box — literally no breaking-in required!
8. A pair of faux leather riding boots that were quite literally made for walking. With a rounded toe, low heel, and criss cross, buckle detailing, these boots are as cute as it gets.
9. A pair of wear-anywhere stacked-heel leather ankle boots because you can easily wear them for hours on end. As a proud owner of Seychelles boots, I can confirm that these bad boys are no joke when it comes to comfort.
10. A pair of chunky mid-calf boots with a slight platform that will look amazing with just about any outfit. Reviewers love that even with the added height, they are super easy to walk in.
11. A pair of quilted knee-high boots with buckle and zipper detailing, for times when you want to walk comfortably with a little bit of throwback preppy style. Plus, thanks to their breathable insoles, this pair will work through fall, winter, AND spring!
12. A pair of ankle boots that were designed to fit like a glove — seriously. Made of textured ReKnit fabric, these shoes were made with the perfect amount of stretch and stability for all day comfort.
13. A pair of slouchy, mid-calf zip-up flat boots, for the days where even a kitten heel feels like too much. Oh, and since they are nonslip, you will be good to go even when the weather turns.
14. A pair of classic, easy-to-slip-on, mini Ugg boots that will likely become your go-to pair of shoes this winter. Since these boots are lined with sheepskin, they are sure to keep your feet warm, no matter how low the temperature drops.
15. A pair of stylish ankle booties because they effortlessly combine a classic Western feel with a city modern silhouette, with their short, chunky heel, trendy ankle slit, and back zipper.
16. A pair of heeled leather combat boots with durable, metal zippers and chunky outsoles that will look good (and feel good) for years to come. No matter how many pairs of shoes I own, I always find myself reaching for these.
17. A pair of snakeskin booties with a chunky block heel, so you can feel like a badass every time you put them on. Despite having a bold pattern, the neutral colors makes them perfect for mixing and matching with a variety of outfits.
18. A pair of knee high boots with a side zipper that I am pretty sure were created with the sole purpose of strutting your stuff.
19. A pair of sparkly ankle boots, because sometimes, you just want to wear a literal disco ball. These Betsey Johnson shoes are a must-buy for anyone who loves a little glitz and glam — they'll absolutely be compliment magnets, wherever you go.
20. A pair of ankle boots with soft, synthetic outsoles, so you can wear them for hours on end. Available in black, burgundy, and caramel, these ultra-comfy boots have a round toe, criss cross straps, buckle hardware, and a low heel — so you'll look like you're on the cutting edge of fashion, but feel like you're wearing your fave broken-in sneakers.
The reviews for this post have been edited for length and clarity.
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