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Unless otherwise specified, all sizes in this post are listed in women's.
1. A pair of Ugg-like, mid-calf suede boots because they're priced about $100 less than the brand name and come in so many colors — from hot pink to burnt orange to your classic, camel suede.
2. A pair of ankle booties that feature memory foam insoles, so you can wear them morning to evening without having to soak your feet in an ice bath afterward.
3. A pair of rainboots for the rainiest and slushiest winter days. These puppies are waterproof and stop mid-calf so your tootsies stay dry. Plus, they're slip-resistant so you don't have to worry about taking a tumble on sneaky ice patches.
4. A pair of fuzzy boots so snazzy, everyone will think you had them custom made by a reputable designer. The twist? You spent less than $100.
5. A combat boot to pair with leggings, an oversized sweater, a leather jacket, and a snuggly scarf. Bonus: they're made with memory foam insoles to keep the blisters away.
6. A pair of cozy boots you can wear during all the fun, winter activities — from visiting the holiday market to sledding to running around in a good ole' fashioned snowball fight.
7. A pair of lace-up booties polished enough for the office, and stylish enough for hot toddies with friends at the local bar.
8. A pair of comfortable booties featuring shock-absorption technology and arch support so your daily trudges to the office in the winter get a bit comfier. *Immediately adds to cart*
9. A pair of ankle boots designed with waterproof faux leather and a block heel so you can wear them both inside and outside this spooky season.
10. A pair of cute, knitted boots so versatile, you can wear them both by the fire roasting marshmallows in your living room or wandering the outdoor market looking for holiday gifts for your BFFs.
11. A pair of sheepskin boots because they're a timeless classic and whether you're a student or going to the office every day, these have you (and your feet!) covered.
12. A pair of Timberland boots because your feet will stay dry, even if you spent 10 minutes splish-splashing around in puddles of slush on your way to meet your friends for drinks.
13. A pair of insulated boots for the winter hikers, sledders, snowmobilers, and bobsledders out there.
14. A pair of heeled boots to effortlessly ~elevate~ your winter wardrobe. These would look great with jeans, a tucked-in turtleneck, and a suede, lapel peacoat. Just sayin ¯\_(ツ)_/¯.
15. A pair of suede lace-up boots because they're made with a non-slip, rubber sole that can easily tackle slippery ice patches or chilly hikes.
16. A pair of waterproof winter boots I'd love to see paired with your best denim, a plaid shacket, and a yummy pumpkin spiced latte.
17. A pair of warm boots as stylish as they are comfortable. These are begging to be worn with leggings, a tee, and an oversized knit cardigan atop.
18. A pair of Chelsea boots you can dress up or down depending on your mood — wear them with a sweater dress for brunch with the gang or with jeans, a tee, and a moto jacket for a casual day out shopping.
19. A pair of stylish boots so chic, your friends will think you spent a month's paycheck on them (spoiler: you didn't). These will be perfect for your lunch date with your S.O.
20. A pair of moto boots that offer good traction on all types of terrain — icy sidewalks, loose gravel, or muddy grass. These will cover you no matter what your winters look like.
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