Get Stuff We Love
From the mod Chelsea boots of the swinging '60s to the chunky, military-inspired styles of the '90s, ankle boots have been a reliable and practical part of our wardrobe for decades now. The true beauty of the ankle boot is its versatility: They work as well with jeans and a T-shirt as they do with dresses and skirts.
Get Stuff We Love
Ahead, we've gathered 33 pairs of fall ankle boots that are cool, wearable and worth the investment. Now go get them!
Block heel ankle boots
A pair of black leather ankle boots with a sturdy (not too short, not too tall) block heel might just be the most essential footwear in your closet. We believe every woman should have a pair of these to wear with everything from skinny jeans and sweaters to dresses and leather jackets.
1. H&M ankle boots, $35
2. ASOS leather ankle boots, $77
3. River Island patent ankle boots, $80
4. Topshop heeled ankle boots, $65
5. Sole Society ankle boots, $55 (originally $109)
6. ASOS leather heel sock boots, $88
7. H&M ankle boots, $50
Suede ankle boots
Suede has more of a casual feel than leather, even in black. Whether you choose a cowboy-inspired bootie or a more urban silhouette, these ankle boots are ideal for weekend wear.
8. Zara elastic split ankle boots, $90
9. ASOS suedette ankle boots, $41
10. H&M ankle boots, $35
11. Plume By FarylRobin suede tassel boots, $60
12. BCBGeneration suede ankle boots, $98
13. Arturo Chiang ankle boots, $99
14. Sole Society western ankle boots, $90
15. H&M lace-up suede ankle boots, $50
16. Sbicca buckle strap ankle boots, $90
Inspired by the boots worn by dapper men in the 1960s (most notably: The Beatles!), the Chelsea boot is back. These classic boots look modern when worn with patterned tights and a flow-y dress.
17. Zara stretch leather ankle boots, $90
18. Topshop Chelsea boots, $70
19. H&M Chelsea boots, $35
20. ASOS Chelsea boots, $62
21. Faith leather Chelsea boots, $73
22. H&M suede Chelsea boots, $35
23. River Island Chelsea boots, $62
Fun colors and fabrics
If your wardrobe already has the basics covered, why not branch out a little? Velvet is one of the trendiest fabrics of the season, but you’ll also find metallic hues, embroidered boots, patent leather textures and even python prints. Wear these not-so-basic booties with your favorite jeans for an unexpectedly rock 'n' roll vibe.
24. Steve Madden velvet ankle boots, $90
25. Journee Collection faux suede lace up boots, $50
26. River Island glitter block heel ankle boots, $80
27. Sole Society heeled ankle boots, $99
28. New Look front zip ankle boots, $49
29. ASOS metallic ankle boots, $52
30. ASOS snake print ankle boots, $62
31. Topshop embroidered boots, $70
32. Public Desire patent ankle boots, $57
33. River Island leopard print velvet ankle boots, $80