19 Things to Wear with Your Ankle Boots

Winter, spring, summer, fall: No matter the season, these versatile shoes add the perfect hint of put-togetherness without all the fuss of heels. Here, 19 things (you already own) that you can wear with your trusty new booties.

How to Wear Ankle Boots (You Might Be Doing It Wrong)

ankle boots with black turtleneck
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Black Jeans, A Black Turtleneck And A Black Blazer

Boots don’t necessarily need to be the last accessory you add. They can be the statement all on their own. Rock your leopard or snakeskin booties with all black to make them pop. Or choose your black booties for a chic, monochromatic look. 

white jeans light sweater ankle boots
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White Jeans And A Light Sweater

Another streamlined look that's effortlessly stylish. Even your plain caramel joints can stand out here.

black jeans with ankle boots oatmeal sweater camel coat
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Black Jeans, An Oatmeal Sweater And A Camel Coat

If you’re going to mix colors, just make sure to coordinate like hues up top and like hues down below. That way you don’t appear too jumbled.

ankle boots with flared denim
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Flared Denim And A Sweater Or Sweatshirt

Sure you can technically sneak knee-high boots under your new flares, but avoid the bulk with an ankle pair. Then keep the rest of the outfit light with a sweater.

statement coat with ankle boots
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A Statement Coat And Trousers

Don’t fear patterns. Boots anchor a loud outer piece.

ankle boots withcuffed jeans
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Cuffed Jeans

Rips are optional.

ankle boots with skinny jeans
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Skinny Jeans And A Long Jacket

Proportions. Proportions. Proportions.

fur jacket sweatshirt ankle boots
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Dark Denim, A Cozy Sweatshirt And A Furry Jacket

This is basically the ideal outfit for brunch with the girls.

ankle boots with teddy bear coat
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Black Jeans, A Black Sweater And A Teddy Bear Coat

This stubby fuzzy material is one of the biggest trends of the year. Pair it with your black ankle boots (and black everything else) for a sleek combo.

turtle neck midi skirt with ankle boots
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A Turtleneck And A Midi Skirt

Showing off a bit of calves is still sexy, people. 

ankle boots with long dress
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A Long Dress And An Oversize Jacket

A long shift, an equally long sweater or jacket and a pair of pointed booties create a super slimming effect.

ankle boots with velvet dress
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A Velvet Dress And A Blazer

This is how you toughen up a going-out look.

black dress with ankle boots
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A Shift Dress And A Moto Jacket

But don’t feel beholden to one specific material. Any little dress can work.

ankle boots with lace dress
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A Lace Dress

Super sweet meets super chic.

ankle boots with red silk pants sweater
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Silk Pants And A Slouchy Sweater

You may think that clunky ankle boots and a flowy silk pants is a bit too much. But that’s where a pink pullover comes into play—to balance it out. 

ankle boots with black culottes
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Culottes And One-shoulder Top

Remember what we said earlier about proportions? Here, you want to make sure your cropped pants are the star of the show. Choose a blouse that hits right at the waistline and let a sliver of ankle show.

boxy sweater culottes ankle boots
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Culottes And A Boxy Sweater

You can also choose a sweater that hits a teeny bit lower (just make sure it’s not hugging your hips) and boots that hit a teeny bit higher.

cotton dress ankle boots bomber jacket
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A Cotton Dress And A Bomber Jacket

Come spring, this ensemble will be your go-to. Just remember to color-coordinate accoutrements.

ankle boots skater skirt cotton t
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A Cotton Tee And A Skater Skirt

Boots with a chunky heel add just enough oomph to a simple grey top and summery skirt.


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As Director of Branded Content at Gallery Media Group, Roberta helps oversee the ideation and execution of sponsored content and experiential campaigns across PureWow and ONE37pm...