19 Ways to Wear Ankle Boots With Literally *Any* Item In Your Closet
They're basically the most versatile shoe, ever.
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Ankle boots keep the world spinning on its axis (okay, we kid, although it's pretty much true) because they're so comfy and versatile — but it can feel tricky figuring out exactly how to wear ankle boots. They may be the go-to fall shoe, but how do you tuck your pants into your boots? Over? Under? Or do you leave them untucked? Can they be worn with sweats, or should you save ankle boots for shorter hems and dressier occasions?!
If those questions sound like your inner monologue as you're standing in front of your mirror and getting dressed in the morning, these tips and tricks for how to wear ankle boots are for you. Whether it's cuffing your jeans, pairing grunge-y boots with soft fabrics and hues, or leaving a little space between your hem and the top of your shoes, here are some genius, celebrity-loved outfit hacks to show off your favorite boots. These tips and tricks will help you style every ankle boot in your closet — cowboy, lug sole, snakeskin, and rain — to prevent them from turning into That Pair You Bought But Never Wore.
Pair with Leggings
Yep, you can totally wear leggings with booties. Let this street style star be a lesson to us all: tighter pants or leggings won't bunch at the hem like other pants will, even if you're wearing a slim-fit ankle boot. Voila — awkward scrunch avoided.
What you'll need: Arely Bootie, $69.99, Journee Collection
Long Skirt + Short Boots
Showing a little ankle is the key to making your boots pop. A little bit of skin draws the eye and breaks up your look, especially if you're wearing a layered outfit like this sundress and button-up combination.
What you'll need: Leather Ankle Boots, $67.98, Amazon
Coutgo Leather Ankle Boots
Opt for Dressy Comfort
Ankle boots are just as stylish as a pair of high heels, and they're way easier to walk in. Give your feet a break the next time you wear a fancy dress and swap the stilettos for a comfy heeled boot.
What you'll need: White Chunky Heel Ankle Booties, $47.99, Dream Pairs
DREAM PAIRS White Chunky Heel Ankle Booties
DREAM PAIRS White Chunky Heel Ankle Booties
Stack with Socks
Before you drop a bunch of money on no-show socks that just end up slipping off your feet (😓) as you walk, try pulling on a pair of crew socks and pushing down the tops right above your boots to create a laidback look.
What you'll need: Rainy 2 Rain Boot, $49.99, Marc Fisher
Go Utilitarian
You'll be able to kill two birds (style + function) with one stone thanks to the traction soles of these heeled ankle boots that are perfect for navigating snowy, slippery weather.
What you'll need: Low Chelsea Boot, $200, Ganni
Add a Fresh Burst of White
When the rest of your outfit is patterned and super bold, try an extra fresh shoe like these bright white ankle booties. They're super versatile, and you might find yourself reaching for them more often than you'd think.
What you'll need: Heel Zipped Boots, $59.99, Mango
Create a Colorblocked Concept
Make a standout colorful detail from your outfit (like the red "P" on Barbara's sweatshirt) pop even more by reintroducing that same color once more via your shoe game.
What you'll need: Mid Calf Rain Boots, $33.99, Evshine
Pair With a Suit
Reach for a graphic tee and ankle booties the next time you're trying to tone down a dressy suit. Opt for a wide-leg pant to slip over your ankle boot. If you weren't able to hem your pants before wearing them out, a little heeled boot will balance out the excess length.
What you'll need: Black Hutch Boots, $99, Steve Madden
Go Grunge
Pair a chunky boot (we're talking about your best stomping boots) with a midi skirt for that effortless vibe. Achieve the sandwich effect by matching your belt and shoes with an unexpected white skirt.
What you'll need: Church Quad Leather Platform Monkey Boots, $179, Dr. Martens
Dr. Martens Church Quad Leather Platform Monkey Boots
Dr. Martens Church Quad Leather Platform Monkey Boots
Stay Balanced with Chunky Boots and Soft Fabrics
When your entire outfit is silky and cozy, add a pair of chunky lug sole boots for that street style star look. A work boot or thicker platform sole will counter some of the sweetness.
What You'll Need: Caled Platform Bootie, $59.99, Marc Fisher
Marc Fisher LTD Caled Platform Bootie
Kelsey is Seventeen.com's fashion expert and resident Harry Potter nerd. At the office, she spends her day writing about style, beauty, and literally every move Kylie Jenner makes. On the weekends, you can find her sifting through vintage shops and hunting for the perfect burger. Follow her on Instagram at @klstieg.
Hannah is the assistant shopping editor at Cosmopolitan, covering all things from cute apartment decor to trendy fashion finds, TikTok products that are actually worth your $$$, and the perfect gift to buy for your boyfriend's mom. She previously wrote for Seventeen and CR Fashion Book. Follow her on Instagram for hot takes on red carpet fashion and unhinged updates on the books she’s reading on the train.
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