20 Best Ankle Boot Buys for Fall

Ankle boots have become a favorite for their versatility and wearability throughout all seasons. They can look bohemian during the warmer months, with a midi dress and a crossover bag, but they can also hold against the elements as you’re heading for work during colder days. They’re practical, comfortable and chic. In other words, the perfect fusion of comfort and style. So if there’s one shoe style you need to add to your closet, this is the one! 

Of course, there are ankle boots for fall in every taste and budget, so finding the right pair shouldn’t be a difficult task. Nevertheless, we’ve rounded-up 20 great pairs to give you a head start! You’ll notice that this season is a combination of retro, 80s-style booties (think pointy toes, animal prints, high heels), modern hiking and western boots for urban adventures, and super-comfortable, sneaker-inspired styles. And then, of course, come the timeless ankle boots that never go out of fashion: Chelsea boots, lace-ups, zippered booties. Ready for your new shoe uniform? 

20 Best Ankle Boot Buys for Fall

Flat Ankle Boots

If you’re all about comfort, flat ankle boots are the choice for you! You can opt for a timeless Chelsea style in a neutral color if you want something that goes with everything. But if you’re after something special, you can’t go wrong with animal print!

1. Madewell The Ainsley Chelsea Boot | 2. Matisse Animal-Printed Ankle Boots | 3. New Look Wide Fit flat ankle boot in gray | 4. ASOS April leather chelsea boots in tan

Heeled Ankle Boots

For the office or even for the holiday parties, heeled ankle boots are the perfect combination of style and warmth. Go for a chunky (even rounded!) heel to make the most of new heights, while still keeping comfortable. 

5. ASOS Romeo pointed heeled boots in black snake | 6. Sole Society Paperbag Bootie | 7. H&M Block-heeled Ankle Boots | 8. & Other Stories Leather Round Toe Ankle Boots

Vegan Ankle Boots

Not a fan of real leather? We get it! Luckily, there are plenty of vegan alternatives these days, just as trendy and just as durable! We picked very different styles, so you can probably find the vegan booties of your dreams below.

9. BC Footwear Azalea Vegan Crisscross Bootie | 10. Native Shoes Fitzsimmons Treklite | 11. Free People Vegan Ranch Boot | 12. Target Kamari Seasonal Sneakers Boots

Waterproof Ankle Boots

While suede and other soft, easy to wear materials have their merit when you live somewhere warm, other places require waterproof footwear for fall. Gorgeous gummy boots – check. All weather Timberlands – check. Flat ankle boots you actually want to wear – also check!

13. Madewell The Chelsea Rain Boot | 14. Timberland Nellie Waterproof Chukka Boot | 15. Sorel Emelie Chelsea | 16. UGG Aureo II Waterproof Bootie

Lace-up Ankle Boots

We gotta give it to lace-up ankle boots: they’re not just timeless, they’re also great for non-standard foot widths! We love zippers and elastic for convenience, but only a lace-up style can truly adjust to your feet!

17. Target Lucia Microsuede Lace-Up Heeled Ankle Booties | 18. H&M Pile-lined Boots | 19. Target Women’s Karri Lace Up Hiker Boots | 20. ASOS Ripple chunky lace up boots in tan