How to Wear Ankle Boots

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Ankle Boots Are Essential This Time of Year!

Getty Images: Christian Vierig

We probably don’t have to tell you by now that ankle boots are probably the most essential footwear trend for fall this season, and probably has been for the past five years at least. We love ankle boots as much for their practicality as their versatility.

For a long time it felt like ankle boots were really only meant to be worn with your skinny jeans, or hiding under a pair of flares — and if you wore them with a skirt, tights were a must. But fashion rules are meant to be broken, and trendsetters around the world have helped usher in a new era for the ankle boot (or bootie) when you can wear yours with… Anything.

Ahead, we’ve isolated four ways to wear your ankle boots this season, from traditional pairings with jeans and sweaters to something unexpected — like a midi dress or a mini skirt with bare legs. See how street style stars are wearing their fall ankle boots and shop our favorite pairs.

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Go Monochromatic... With Any Color

Getty Images: Christian Vierig and Kirstin Sinclair

Yes, yes, head-to-toe black will always look good. A black blouse with black skinny jeans and black ankle boots with a heel is an outfit recipe to look as long and lean as possible. But don’t forget the other colors of the rainbow — ones that can give you a whole new perspective on the appeal of a monochromatic ensemble.

Haven’t ever considered wearing a full look of brown, oatmeal and rich chocolate hues? The effect is strikingly cool and unexpected — and of course appropriate for the fall mood.

Burgundy is another autumnal hue that will look good from top to bottom. You can keep it simple though — just a dress and booties in the same hue feels fresh. Also consider navy or shades of gray for this look (but don’t expect to find a way to wear all 50!).

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Try an Unexpected Color or Texture

Getty Images: Christian Vierig, Timur Emek and Edward Berthelot

Ankle boots have become so ubiquitous for that designers and mass market retailers alike are experimenting with all kinds of colors and textures, giving everyone — street style stars and us regular people alike — a chance to really get creative with our fall footwear.

If you're not so adventurous when it comes to dressing, simply breaking away from black or brown to try something like grey, deep oxblood or something in a neutral metallic like gold or silver. Trust us — with a pair of mid wash or black jeans and your favorite cozy sweater you can pull them off easily. (And at just about any age, we promise!)

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Try Ankle Boots With Unexpected Hem Lengths

Getty Images: Melodie Jeng, Timur Emek and Kirstin Sinclair

Ankle boots with cropped jeans? Yes! If you're an adventurous dresser and looking to try a style that's a little bit unexpected, we love this look. For those who are maybe a little more timid about showing bare leg with your ankle boots, ease into it with a playful mini skirt or even a maxi dress with a slit.

You might want to try on a variety of boots that stop at a different spots on your ankle or calf, in order to find a look that is most flattering for your legs — that way you'll feel confident trying something a little outside the box.

For extra style points, try a scarf with your look!

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The Skinny Jeans Pairing Is Always In Style

Getty Images: Daniel Zuchnik and Christian Vierig

Ah, the classic. Our favorite leg-lengthening way to wear ankle boots is with skinny or legging-style jeans. This look is currently very on-trend and will make you feel even longer and leaner than flare jeans paired with heels. For the most streamlined look, match your boots and jeans — aka black on black.

We love this ankle boots outfit idea most of all because it works for any age and pretty much any body shape, too. (Here are the best jeans for every body type, by the way.) You can wear your skinny jeans and ankle boots with a tunic (to conceal wider hips) with an oversized sweater (very collegiate) or just a pretty blouse (date night anyone?) and you'll be good to go.