How to Wear Ankle Boots

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Cowboy, Baby

Get a head start on fall's Western trend by styling a pair of cowboy ankle boots with a long-sleeved dress.

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Paris Texas Shop the Look: Lovely Western Boots

Paris Texas Shop the Look: Lovely Western Boots

Paris Texas's classic cowboy ankle boot is the perfect way to add a little edge to all your dresses and skirts.

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The Trouser Tuck

For a chic way to show off your footwear, tuck a pair of trousers into the tops of your boots.

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Jimmy Choo Shop the Look: Suede Boots

Jimmy Choo Shop the Look: Suede Boots

Now 50% Off

A higher ankle boot can be easier to style with pants and midi-length dresses. 

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White Contrast

Contrast a colorful print dress with a pair of stark-white booties for an unexpected pop.

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Off-White Shop the Look: White Ankle Boots

Off-White Shop the Look: White Ankle Boots

Now 50% Off

Pair Off-White's white bootie effortlessly with all your fall dresses.

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Sleek and Sexy

Style a pair of stiletto ankle boots with blue jeans and a blouse for a look that can go from day to night à la Kendall Jenner.

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Balmain Shop the Look: Leather Ankle Boots

Balmain Shop the Look: Leather Ankle Boots

A luxe boot that will make you feel 10 times sexier on a night out.

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Touch of Snake

Top off a menswear blazer and boyfriend jeans with textured ankle boots that add dimension. This season, we're feeling snakeskin for a break from our go-to black boots.

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By Far Shop the Look: Snake-Print Boots

By Far Shop the Look: Snake-Print Boots

Featuring a subtle lace-up detail, By Far's snake-effect boots add a touch of cool to any look.

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Pair Them with a Slip Skirt

Take your favorite slip skirt from summer to fall by styling it with a pair of sleek, pointed-toe booties.

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Acne Studios Shop the Look: Jensen Leather Ankle Boots

Acne Studios Shop the Look: Jensen Leather Ankle Boots

Acne's pointy-toe boots can be shown off when worn with a slip skirt or pair of jeans.   

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In the Nude

While we love classic black or white ankle boots, a light nude color makes for a chic, unexpected alternative that will go with virtually everything in your closet.

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Gianvito Rossi Shop the Look: Nude Leather Ankle Boots

Gianvito Rossi Shop the Look: Nude Leather Ankle Boots

Now 49% Off

Gianvito Rossi's neutral ankle boot is both minimal and elegant—and sure to stand out among a sea of all-black booties. 

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Make It Shine

Patent ankle boots pair perfectly with denim—whether you want to wear them with a midi skirt or pair of jeans.

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Dear Frances Shop the Look: Patent Cape Ankle Boots

Dear Frances Shop the Look: Patent Cape Ankle Boots

Add a little shine with Dear Frances's subtle patent boot that is the perfect amount of shine for daytime and pairs perfectly with denim. 

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Midi Dressing

Ankle boots and midi-length hemlines make for the ideal transitional outfit combo. When the temperatures drop, top your look off with a trench.

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Alexandre Birman Shop the Look: White Jean Booties

Alexandre Birman Shop the Look: White Jean Booties

Score Alexandre Birman's bootie while it's still in on sale and then proceed to wear it with all your fall looks—from midi dresses to skinny jeans.

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Schoolgirl Days

Transition your miniskirt to fall by wearing it with a pair of textured tights and boots.

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Chloé Shop the Look: Snake-Effect Ankle Boots

Chloé Shop the Look: Snake-Effect Ankle Boots

Now 60% Off

High shine, rich texture, and the ideal walking heel: This luxe boot not only looks cool with a miniskirt, but just about everything else in your wardrobe too.  

Jaclyn Palermo is a Fashion Editor with the Hearst Fashion Group, specializing in accessories. Standing under 5 feet, she’s never afraid to make a big fashion statement, preferably at an art opening, and is always on the hunt for the perfect vintage home find in Brooklyn. Follow her on Instagram@j_palermo.

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