Unless otherwise specified, all sizes in this post are listed in women’s.
1. A pair of classic faux-suede knee-high boots from Anthropologie with leather insoles you'll be able to wear year after year and never get sick of.
2. A brown suede knee-high boot from Torrid just begging to be worn on a chilly autumn day while listening to "All Too Well (Taylor's Version)" and sipping a PSL.
3. A pair of black leather Steve Madden knee-high boots adorned with silver studs and laces to ~tie together~ all the edgy vibes these babies emanate.
4. A slouchy flat knee-high boot for you to pull on when you know you'll be walking a lot (through a corn maze, perhaps?) but still want to rock some stylish kickers.
5. A pair of brown leather knee-high cowboy boots by Lane Boots boasting gorgeous whipstitching down the sides and memory foam footbeds so you can comfortably wear them to your next country concert tailgate.
6. A chic chunky knee-high heel boot designed with a padded faux-fur lining and insole that might just make you wish you could wear winter fashion year-round.
7. A pair of knee-high snow boots fully equipped with all-weather insulation, a faux-fur interior, and breathable uppers to help you take on those freezing temps while still feeling cute 'n' cozy.
8. A black knee-high platform boot by Lucky Brand to rock with whatever you want because these are super versatile and deserve to be worn with everything in your closet.
9. A chunky knee-high lace-up boot from Asos that'll hug your calves as you listen to Avril Lavigne's new single and reminiscence the days when you'd listen to her on Hit Clips.
10. A pair of sleek leather knee-high heel boots from Franco Sarto to wear while filling your kitchen cabinets with enough apple cider donuts to feed a family of 10.
11. A pair of cozy knee-high Ugg boots complete with soft knitting and adjustable side straps so your feet and calves will feel right at home.
12. A blue faux-leather crocodile-embossed knee-high heel boot from Lulus guaranteed to ~croc your world~ and turn some heads while they're at it.

13. A pair of faux-snakeskin knee-high boots by Vince Camuto with an uncanny resemblance to the ones Raven Symoné wore during the "Strut" scene in The Cheetah Girls 2.
14. A faux-leather knee boot sporting a quilted exterior, stylish zippers and buckles, and a knit finish on the upper calves. In other words, a pair of boots you'll love if you don't mind receiving compliments all day.
15. A black faux-leather knee-high boot from Torrid featuring three stylish buckles and an extra-cushioned footbed destined to be a timeless staple in your shoe collection.
16. A pair of slouchy knee-high, high-heel boots from Vince Camuto you can grab in velvety or croc-embossed suede — aka a foolproof way to add some stylish flair to any outfit.
17. A water-resistant pair of suede Söfft boots embellished with laces running down the backs for an effortlessly stylish look no matter what the rest of your outfit looks like.
18. A pair of Louise et Cie knee-high lace-up boots that are truly the perfect crossover between edgy and chic.
19. An Eloquii knee-high heel boot spotted with polka dots for anyone who *lives for* wardrobe statement pieces.
20. A stylish faux-suede black knee-high boot featuring a block heel and a silver hardware accent guaranteed to make you feel like the main character anywhere you go.
21. A faux-leather or -suede boot (with a pocket!) that'll inconspicuously add 2 inches of height courtesy of its hidden wedge.
22. A black knee-high boot by Naturalizer complete with a block heel and leather exterior — basically, *the* quintessential chilly-weather boot.
You, every time you're faced with a new task in life:
Reviews have been edited for length and/or clarity.