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1. Chelsea boots that, despite having a generous heel, are comfortable enough to walk around in all darn day. These are perfect for weekends fueled by pumpkin lattes, apple cider donuts, and the promise of yet another fall hay ride.
2. Heeled booties embellished with a chunky gold chain, a unique twist on the little black booties you’ve been wearing since high school that — and I mean this in the least offensive way possible — should have probably been retired about three years ago.
3. Columbia hiking boots because perfection really does exist, and it's both stylish *and* functional. Reviewers can't stop raving about the solid quality, out-of-the-box comfort, and awesome traction that these waterproof babies offer.
4. Over-the-knee boots to instantly upgrade your 'fit from "I woke up late this morning" to "I woke up before my alarm, ate an avocado-fueled breakfast, and even had time to shower."
5. 100% leather Chelsea boots brought to you by Dr. Martens, for comfy-but-make-it-badass rocker style. These are lined with faux fur to keep your hooves warm and toasty.
6. A pair of classic Chelsea boots — they epitomize the phrase "wardrobe staple." These babies go with any outfit, contain a five-layer memory foam insole for maximum comfort, and their grippy outsoles mean no slipping and sliding on pavement. Ever.
7. Leather ankle boots with a wooden heel available in a slew of colors and patterns (think everything from brown croc to smooth gray). I don't recommend following the link if you're indecisive — I can almost guarantee you'll add four pairs to cart. Sorry not sorry in advance.
8. Tall boots designed with low impact leather and delightfully comfy padded insoles, the latter of which gets rid of break-in time completely. That's right, folks! You'll be able to walk for miles as soon as your hooves are nestled inside these beauties.
9. Chunky booties that should really start negotiating for PTO now considering you'll likely wear them every darn day. These babies are destined to become the ~little black dress~ of your shoe collection.
10. Slouchy boots noted by one reviewer as being perfect for cropped denim and, wow, yes, these are officially the only shoes I want to wear with my shin-skimming jeans.
11. Vegan ankle boots destined to become the little black shoe of your wardrobe. Perfectly versatile for any season, these babies are ideal for pairing with jeans, dresses, midi skirts, and everything else you plan on wearing... ever.
12. Chunky over-the-knee lace-ups to add polish to any outfit, even if said outfit consists of black leggings and a wrinkled tee. Throw on a black blazer for extra oomph and hoorah! We’re got a recipe for your next #OOTD.
13. Blundstone Chelsea boots appropriate for any kind of activity — think everything from hiking to grabbing your morning caffeine. These premium leather splurges are water resistant, provide solid traction, and have an ergonomically engineered toe spring and a removable comfort footbed.
14. Steve Madden ankle boots bound to become the apple of your eye, the not-so-hidden ~gem~ of your wardrobe, thanks to funky accent gems. Not required but highly rec’d: throw these on with some fishnets to channel The Craft in the best way possible.
15. Ankle boots lined with faux fur to keep your hooves feeling toasty, even when the temps begin to drop and spooky season is in full blast. Consider these an "outdoors approved" version of your favorite house slippers.
16. Waterproof leather Converse for a fashion-forward twist on their classic Chucks. These are designed with a cushy memory foam lining for maximum comfort, so I impart on you a warning: You will want to wear these trendy pals every. single. day.
17. Vagabond Shoemakers heeled boots featuring a square toe and block heel that are versatile enough for daily wear, but funky enough to stand out amongst the seaaaaa of other booties residing on the floor of your cramped closet.
18. Thigh-high boots that are the perfect compromise: They look ultra-dressy but manage to be unbelievably comfortable, ergo you can look chic *and* put together without having to feel like you're wobbling around on stilts.
19. Kenneth Cole knee-high boots for shoe game that always delivers. These beauties are capable of making any 'fit look runway ready thanks to their chunky heel and chic faux-leather construction.
20. Micro-suede ankle booties that require minimal break-in time — just take 'em straight out of the box, put them on your feet, and be on your merry way.
21. Ugg shearling-lined boots considered ~classique~ for a reason. These babies are basically an extension of your favorite slippers, the difference being you can actually wear them outside of the house, thanks to a grippy outsole and pretreated suede.
22. Kamik waterproof boots you can drag through snow, sleet, rain, and mud, but rest assured that your hooves will remain perfectly warm and dry. These are fantastic for the colder months that are (unfortunately) approaching, plus great for hiking rough terrain.
23. Knee-high combat boots lined with faux fur to keep your legs and tootsies feeling nice, warm, and toasty — even when the weather outside can best be described as "my face hurts." A personal aside: I won't miss summer humidity, but I'm also not looking forward to freezing my assets off.
24. Joules rain boots available in a *ton* of fantastic colors and prints: we're talking stripes, polka dots, botanical bees, and French bulldogs galore. I wish you luck on your journey of choosing just one of the 18 available options.
25. Waterproof Vionic ankle booties designed with an orthotic arch that hugs your foot in a way that offers comfort and support. Throw in a classic style and ding ding ding, you've got yourself a contender for the perfect staple shoe.
26. Cozy slip-on booties equipped with a chunky heel and fuzzy inner lining for comfort, plus an adjustable shaft that basically means you'll be purchasing *two* pairs of adorable shoes for the price of one.
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