How To Wear Ankle Boots: 6 Genius Styling Tips + Our Favorite Pairs

January 8, 2015 by Claudia Saide
shefinds | Style
view slideshow

If you were one of the millions that Googled “How to wear ankle boots” in 2014, we heard you loud and clear—styling ankle boots can be tricky and we’re here to help. Since ankle boots can be worn year round, there are literally endless ways to wear them, with mini skirts and bare legs to coated denim and sweaters.  They’re probably the most versatile shoe out there—just about anything goes with them. We figured you’d want to know exactly what we mean by that, so we put together some tips and outfit ideas to address all your curiosities. Just read through the list, and click through the slideshow, and you’ll become an ankle boot wearing pro. Ready, set, go!

Pair them with all your favorite clothes. Celebs like Rachel Bilson wear ankle boots with everything from denim cutoffs and t-shirts to boho dresses and boyfriend jeans—you can do the same. Just decide what you’re in the mood to wear, because like we said before, anything goes, especially since you can wear them when it’s hot or cold. Perhaps you’d like to wear them with leather leggings, flirty dresses, mini skirts, shorts, joggers, cropped trousers, boyfriend jeans, or even sweatpants—all work.

Know when to tuck and when to cuff. Here’s where things might seem a little tricky—since pants can be styled in several ways, they might be an intimidating thing to wear with an ankle boot, but just figure out what type of pants they are, and go from there. Are they cinched, slouchy, super tight, or skinny? If so, try tucking them into ankle boots—the look really works. But if you’re wearing jeans, definitely cuff them—cuffed jeans and ankle boots are, like, the perfect couple.

When in doubt, wear something cropped. Cropped pants are another great mate to ankle boots, especially since you don’t have to think about what you’re gonna do with your pant bottoms.

Wear cool socks. Socks are a fun way to accessorize ankle boots, as long as they’re not your plain looking gym socks. If you’re wearing cropped pants or cuffed jeans, just pull the socks up so they peak out right above the ankle boots.

Pick the right pair for you. What’s super important is knowing what type of ankle boot suits your personal style, because there’s a big difference between an Isabel Marant Dicker Boot and a pair of Saint Laurent chelsea boots—one screams boho while the other is super polished. So when you begin your search for the perfect pair (or pairs, if you’re anything like me), you should first figure out how you’d like to wear them. Are you the boyfriend jeans and baggy sweater type, the girl in black tights and a super short skirt, or the overalls and beanie wearing chick? All of the above? See the Rag & Bone Newbury.

Know the master brands. Certain brands do ankle boots better than others, with Rag & Bone being the perfect example—their Newbury boot comes back year after year, and everyone from Jessica Biel to Sienna Miller and Rachel Bilson (told you she’s obsessed) has been seen in them. The thing with these is that they work on anyone—the hipster, the bohemian, the rocker, even the girly girl—you’d be hard-pressed to find a girl that didn’t look cool in a Rag & Bone Newbury.

Then there’s Acne Studios—they’re known for the Pistol and the Jensen ankle boots—their quality of leather is like no other. If you’re a fan of their moto jackets, you’ll likely love their ankle boots.

This season in particular though, Saint Laurent and Givenchy took ankle boots to a whole new level. The Saint Laurent Cat Appliquéd Suede Boot is so good that it was on Elle’s list of 30 Must Have Ankle Boots, and Givenchy’s Laura Chain-Trimmed Leather Boot was seen on It girls like Chiara Ferragni and Kendall Jenner. Don’t even bother trying to find either one on sale, it’s never gonna happen—totally worth the splurge though.

Before you go, don’t forget to look at the gallery—it not only illustrates some of what you just read, but there are also 10 outfit ideas and a variety of the season’s best ankle boots that you can still get your hands on—because once you see how to wear them, you’ll be wanting them even more than you did before.

[Photo: Cheetah is the New Black]


From Our Partners

Learn more about RevenueStripe...

From Our Partners

Learn more about RevenueStripe...


This Twist Front Top Is The Flattering Fall Essential Every Woman *Needs* In Her Wardrobe

The silver lining of summer winding down? Fall fashion, of ...


This Is The Cute And Flirty Little Black Dress That's Missing From Your Closet

When it comes to building a timeless closet, there are ...


8 Pieces We Have Already Started Buying For Fall

Fall is hands-down our editor's favorite season when ...


Psst! Snag This Super Cute adidas Sports Bra While It's On Sale For Just $14 Right Now

Calling all exercise enthusiasts! Drop what you're doing and ...


5 End Of Summer Steals Under $25 You Don't Want To Miss

We never like to say goodbye to Summer. It means ...


Sarah Jessica Parker Looks So Good In Intimissimi's New Bra Twist Collection--We Want *Everything*

New season, new lingerie! Your fall fashion checklist shouldn't ...


Nordstrom Shoppers Love This $35 Maxi Dress--It's So Pretty And Comfortable, Too

With summer winding down, there's one thing you need ...


This $29 Halter Dress Looks Good On *Every* Woman

Drop what you're doing and get over to...


You Can Stop Looking--This Is The Perfect Tee (And It's On Sale Right Now!)

As someone committed to looking good without sacrificing comfort, I'...


Score This Gorgeous Embroidered Tank While It's On Sale For 50% Off At Nordstrom

Despite all the back-to-school messaging everywhere you look, ...


Drop Everything! Natori's Bestselling Feathers Contour Bra Is 50% Off Right Now

Most women don't update their lingerie drawer often enough, ...


This $29 Wrap Top Comes In Sizes XS-4X--And It Really Looks Good On *Every* Woman

If you're looking for the perfect transition piece that ...