Stride stylishly into fall with the season’s most-coveted footwear silhouette: the ankle boot.
Sleek, chic and easy to wear, this versatile style will take you from the school drop-off line to date night and everything in between. TODAY Style scoured the market for the best booties out there, from timeless to trendy, so you can step up your footwear game with a simple click of a button. And with all pairs less than $50, you can get that well-heeled look without breaking your budget.
Polished
Look ready for anything with these sophisticated ankle boots. Sleek and understated, these power pairs exude executive polish and a get-it-done attitude — no expense account required.
1. Melissa Shoes ‘Drama’ Boots, $40, 6pm

2. ALDO ‘Eliliane’ Peep-Toe Boots, $41.50, Selfridges & Co.

3. Clear-Heel Boots, $50, Zara

4. ‘Faye’ Sock Boots, $50, Boohoo

5. Pearl-Detail Boots, $47, SheIn

6. 'Make a Wild Stride' Boots, $49, ModCloth

7. Simply Vera Vera Wang Faux-Snakeskin Boots, $50, Kohl’s

8. Black Lace-Up Boots, $50, H&M

9. Grommeted Patent Boots, $50, H&M

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Casual
Kick back in these weekend-ready ankle boots, selected for their versatility and wear-all-day endurance. Toeing the line between cozy and cool, these laid-back designs prove that good style never takes the day off.
10. Brogue-Style Boots, $50, H&M

11. Indigo Rd. ‘Chant’ Booties, $40, Century 21

12. LifeStride ‘Puddle’ Boots, $30, 6pm

13. Mia ‘Maylynn’ Knit-Trimme Hiking Boots, $50, Nordstrom Rack

14. ‘Oregon Trail’ Booties, $32, Lulu’s

15. T.U.K. ‘Harper’ Velvet Hiking Boots, $40, Century 21

16. Mad Love Kenzie Lace-Up Boots, $31, Target

17. VOLATILE ‘Axle’ Boots, $35, 6pm

18. Pop ‘Hugo’ Foldover Boots, $45, JCPenney

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Trendy
Be ahead of the fashion wave in one — or all! — of these design-driven ankle boots. From cutouts to color blocks, florals to fringe, these of-the-moment styles will have everyone watching your step.
19. A+ Designed by Aldo ‘Shanel’ Studded Booties, $36, Target

20. Braided Tassel-Tie Boots, $31, Charlotte Russe

21. Circus by Sam Edelman ‘North’ Boots, $42, 6pm

22. Diamond by FarylRobin ‘Fawcett’ Embellished Boots, $40, Target

23. Mo Mo Panda Vintage Bow Boots, $36, Walmart

24. Diba ‘Danica’ Floral Booties, $50, DSW

25. ‘This Is It’ Lace-Up Boots, $39, Lulu’s

26. Pom Pom Booties, $40, SheIn

27. Diba ‘Danica’ Color Block Booties, $50, DSW

28. Chain-Detail Cutout Boots, $43, SheIn

29. ‘Heat of the Moment’ Booties, $43, Windsor

30. New Look Velvet Boots, $49, ASOS

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Classic

32. Elastic-Panel Boots, $50, Zara

33. American Rag ‘Desyre’ Chelsea Booties, $45, Macy’s

34. ‘Grace’ Chelsea Boots, $40, Boohoo

35. Slip-On Boots, $35, H&M

36. New Look Heeled Chelsea Boots, $49, ASOS

37. SONOMA Goods for Life™ Wedge Boots, $40, Kohl's

38. SO® Desert Boots, $40 Kohl’s

39. Lace-Up Booties, $35, Forever 21

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