Ankle Boot Outfit Formulas to Take You from Summer to Fall
Fresh inspiration for how to style fall's footwear MVP.
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It's officially time to start transitioning your wardrobe from summer to fall. And if there's one staple your closet needs, it's the versatile ankle boot. Perfect to wear with dresses, skirts, and jeans, and featuring details from stiletto heels to Western embellishments, booties are the ultimate footwear MVP. Get inspired by some of this season's hottest ways to wear ankle boots.
Cowboy, Baby
Get a head start on fall's Western trend by styling a pair of cowboy ankle boots with a long-sleeved dress.
Paris Texas's classic cowboy ankle boot is the perfect way to add a little edge to all your dresses and skirts.
The Trouser Tuck
For a chic way to show off your footwear, tuck a pair of trousers into the tops of your boots.
A higher ankle boot can be easier to style with pants and midi-length dresses.
White Contrast
Contrast a colorful print dress with a pair of stark-white booties for an unexpected pop.
Pair Off-White's white bootie effortlessly with all your fall dresses.
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.
A luxe boot that will make you feel 10 times sexier on a night out.
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.
Featuring a subtle lace-up detail, By Far's snake-effect boots add a touch of cool to any look.
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.
Acne's pointy-toe boots can be shown off when worn with a slip skirt or pair of jeans.
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.
Gianvito Rossi's neutral ankle boot is both minimal and elegant—and sure to stand out among a sea of all-black booties.
Make It Shine
Patent ankle boots pair perfectly with denim—whether you want to wear them with a midi skirt or pair of jeans.
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.
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.
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.
Schoolgirl Days
Transition your miniskirt to fall by wearing it with a pair of textured tights and boots.
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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