How to Wear Ankle Boots


Once sundress season is over, rocking a pair of Coachella-worthy ankle booties can be tough. Do you tuck your pants into your boots or tuck your boots under your pants? Can they be worn with sweats? What about socks? There are so many boot-related questions that pop up once the fall season hits, all of which have flashed through my head while standing in front of the mirror trying to figure out what to wear.

So to save your favorite ankle booties from turning into That Pair You Bought But Never Wore, here are some genius outfit hacks for showing off your new boots. These tips and tricks will help you style any and every boot in your closet.

Wear Them As A Hero Piece

Make your boots the focal point of your look by layering on cool-girl basics (like a leather blazer and fitted jeans) that won’t steal their shine.

What you’ll need: Yale Chelsea Boot, $89, Marc Fisher

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Keep it Tonal

Not sure what to do with your uniquely-colored boots? Match them up with pieces of the same color for a chic, artsy look.

What you’ll need: Cecy White Pointed-Toe Ankle Boots, $47, Lulus

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Make Your Legs Look SO Long

Let Chanel Iman’s expert pairing stand as a lesson to all of us: high rise leather leggings with matching ankle booties give you giraffe legs.

What you’ll need: Brianna Black Patent Leather Croc Boots, $23, Public Desire

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Pump Up Jeans and a Tee

Wait, Joe Jonas is in this picture? I was too distracted by Sophie Turner’s killer look. Pairing black ankle boots with skinnies and a vintage tee is a forever-stylish move.

What you’ll need: Low-Heeled Sock Style Ankle Boots, $50, Zara

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Wear With a Dressy Look

If Lizzo can wear boots on the red carpet, you can do it to prom, homecoming, watever. They add a cool-girl punch to any fancy look.

What you’ll need: Double Take Two-Tone Boot, $40, Nasty Gal

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Use Them As Your Pop of Color

Bright cobalt booties can be somewhat terrifying, but as Emma Roberts proves, they’re totally wearable. Just pull any piece in your closet that features a similar tone for easy pairing.

What you’ll need: Blue Velvet Pointed-Toe Boots, $53, Lulus

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Put With a Suit

Reach for a graphic tee and ankle booties the next time you’re trying to tone down a dressy suit (but still want to look fabulous).

What you’ll need: Black Patent Leather Platform Boots, $136, Topshop

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Pair Them With Sweats

Remember when I said sweatpants are perfect for any occasion? Well, Zendaya just proved me right. The secret to her unexpected look: she opted for a pant that tapers inward around the ankle so they tuck nicely into narrow boots. If you’re duping her look, be sure to go ultra glam on the makeup/hair to give the whole ensemble a dressy vibe – not just your feet.

What you’ll need: Reward Lace Up Heeled Boots, $64, ASOS

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Cuff Your Jeans

Highlight your favorite fall kicks with this two-second hack. Cuffing your jeans literally frames your boots – plus, it’ll help you hit that perfect bootie-length without cropping your jeans for real.

What you’ll need: Kate Square Toe Boots, $50, Circus By Sam Edelman

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Go for Flares

Kendall Jenner’s favorite pairing for fall: floor-grazing flares with square-toed booties (need). Rock this look for major ’90s feels.

What you’ll need: Black Square Toe Ankle Boot, $68, PrettyLittleThing

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Step Outside Your Color Scheme

Exhibit number 2 for my case that boots and sweatpants are a match made in heaven. Kimmy also presents the compelling argument that a bold shoe will make a major statement next to a one-color outfit.

What you’ll need: Tiana Snake Effect Boots, $32, Simmi London

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Go for a Cropped Jean

Showing a little ankle is the key to making your boots P-O-P. A little bit of skin draws the eye and breaks up your look, so your black-on-black-on-black-on-black outfit doesn’t blend together into one massive dark blob.

What you’ll need: Faux Patent Leather Ankle Boots, $28, Forever 21

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Try a Statement Sock

I’ve long lived by the motto: if Selena does it, I should too. Feel free to adapt it to your own life, especially if you’re currently debating rocking a pair of funky socks with your booties. The extra layer will keep you warm and feels so fall.

What you’ll need: Womens Tabby Block Heel Booties, $80, Chinese Laundry

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Show Some Leg

If a little ankle draws the eye, pairing ankle boots with a short-short will really put them on display. If you’re keeping it simple like Taylor’s classic pairing, go for a shoe with a funky detail like studs or embroidery.

What you’ll need: Sabana Too Bootie, $149, Rebecca Minkoff

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Wear Them With a Slip Dress

Booties and a slip is a typical music festival pairing. Add a studded jacket like Shay’s and you’re ready for Coachella.

What you’ll need: Nina Waterproof Suede Boot, $90, Blondo

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