20 Style Tips On How To Wear Ankle Boots

After a long, cold winter, I was really excited to spend the summer wearing flip-flops and sandals. I couldn’t wait to show off my pedicures and to free my feet. But now, after a long, hot summer, I’m pretty excited to start wearing boots again. Not to be weird, but my feet are kind of gross because flip-flops and the beach will do that to a girl.

Boots my favorite things to wear on my feet. They keep you warm, the right pair looks chic no matter what you’re wearing, and they’re (almost always) comfortable. I especially love ankle boots, because they’re even more versatile than high boots. During the colder months, ankle boots look amazing with jeans, or a skirt or dress with tights. During warmer months, you can get away with wearing the right pair of ankle boots with shorts or a dress. What more could you ask for?

But if you’re new to ankle boots, I can see how they might be a little intimidating. Or maybe you’re just stuck in a style rut and you want some new ideas. Either way, here are 20 style tips on how to wear ankle boots:

 

1. Tackling the midi-skirt trend is easy when you pair one with ankle boots. Add a cardigan or jacket and it’s a perfect fall look. 

how to wear ankle boots

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2. Make use of your summer kimonos by wearing them with ankle boots and leggings or skinny jeans. 

how to wear ankle boots

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3. Make a summery dress work for fall by wearing it with ankle boots and a jacket. 

how to wear ankle boots

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4. Roll or cuff your jeans up so that your ankle peeks out… 

how to wear ankle boots

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5. …Or cuff your jeans into your boots, like so… 

how to wear ankle boots

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6. …Or just tuck your jeans into or right over the ankle boots. Whatever you like! 

how to wear ankle boots

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7. In warmer weather, ankle boots look adorable with a pair of denim shorts. 

how to wear ankle boots

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8. Throw fashion rules out the window and wear your ankle boots with visible socks pulled up and a skirt. Add a leather jacket for some added toughness. 

how to wear ankle boots

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9. Ankle boots look amazing with a maxi dress or skirt. In the colder weather, throw on a jacket or cardigan. 

how to wear ankle boots

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10. Go for a pair of fun, colored ankle boots instead of just brown or black. They will instantly make your outfit so much more unique. 

how to wear ankle boots

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11. Pair ankle boots with jeans, and pull your cutest socks up over them. 

how to wear ankle boots

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12. You can’t go wrong with a dress, cardigan and ankle boots on the warmer days of fall. 

how to wear ankle boots

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13. You also can’t go wrong with a skater skirt, a sweater, tights and ankle boots. So chic and easy! 

how to wear ankle boots

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14. Boyfriend jeans are typically cuffed anyway, which makes them perfect for ankle boots. 

how to wear ankle boots

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15. Make denim shorts work for fall and winter by pairing them with ankle boots and tights. 

how to wear ankle boots

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16. Do lots of fall layering with ankle boots for a really cute look. 

how to wear ankle boots

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17. Leggings and ankle boots are such a comfy match. Add a flannel shirt to be even more comfortable. 

how to wear ankle boots

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18. Break up an all-black ensemble with different colored boots. 

how to wear ankle boots

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19.  Or wear black ankle boots with black tights or pants to elongate your legs. 

how to wear ankle boots

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20. Does any outfit scream “fall” more than ankle boots, jeans, a plaid shirt, a fur vest and a scarf? Nope. 

how to wear ankle boots

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Which of these outfits is your favorite? How do you wear your ankle boots? What kind of style tips do you want to see? Tell me in the comments!

You can follow the author, Jessica Booth, on Twitter or Instagram.

 

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  • Emma

    I can’t decide what I think of your inclusion of the kimono trend (the fact that we’re calling it that and the ones that literally ARE real kimonos feel a little culturally appropriative) but this was a great post! I liked the look with the cute socks and can we get an eff yeah for a all the plus size models here :)