Are Ankle Boots Unflattering? 8 Ways To Style Them If You Love This Classic Winter Staple

Despite multiple fashion assassination attempts, the ankle boot is back and is stronger than ever (what doesn’t kill you). So if your booty loves a bootie, here are eight ways to style the verifiable winter fave.

By Julie Drake3 min read
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The fashion world has feelings about the ankle boot. In fact, if there ever was an appropriate time for an “it’s complicated” designation in regard to a relationship with the controversial style, it is now. Case in point? Entering into the record two pieces of evidence: 1) Morgan Stewart tried to cancel the marginalized piece of footwear last year on the Call Her Daddy podcast. The result? Utter failure. (It may have something to do with the fact that, after the podcast, internet sleuths found a photo of Stewart wearing the besmirched accessory and looking, dare we say, very on-trend.) 2) French girls wear them. And if French girls (our fashion commanders-in-chief) wear them, then so do we. Case closed.

Now that ankle boots have clearly been saved from imminent style death, let’s talk about how to wear them. Because although we’re happy she wasn’t successful in her cancellation attempt, during the aforementioned exchange, Stewart elaborated on how unflattering the ankle boot can be – and she has a point. Indeed, ankle boots worn the wrong way, i.e. too short-shafted or with skinny jeans, can be a major fashion fail (see @stylewithangelica detailing this point beautifully on TikTok, where she advises choosing a boot that hits a few inches above the ankle, rather than below it, which can cut you off proportionally).

So, how to wear an ankle boot in a way that flatters and maintains fashionista status? Let us count the ways:

1. With a Funky Kick Out Crop

French influencer Jeanne Ménard debuted an unexpected pairing of sage velvet kick out crops and a burgundy leather square-toe. Quirky, yet charming. Top it off with a billowy white blouse, and we’ve got a twee Captain Hook vibe that Ménard really should be trademarking. Adorable.

2. With a Mini and a Cardi

Nothing screams naked and unafraid like a miniskirt in winter. Pure dragon energy. (And we thought boys were brave.) Pair it with a slouchy pointed-toe ankle boot and a comfy grey cardi (as seen here by Finnish model Sofia Ruutu), and you’ll be exuding cool – literally and figuratively.

3. With a Wide-Legged Jean

Le proportions have entered the chat. Jeanne Ménard’s wide-legged jeans are just the right width and just the right length to show off these adorable cream block-heeled ankle boots without sacrificing the much sought-after “elongated silhouette.” These particular booties have the added bonus of matching the architecture and, therefore, stealing the show. How Parisian.

4. With Your Shortest Rocker Shorts

French fashion girl Camille of @alixystories says don’t be afraid to rock a little edge from time to time. After all, a dash of tasteful grunge never goes out of style. These “utilitarian chic” square-toe ankle boots are the perfect complement to a band tee and cutoffs. And will no doubt leave a trail of fanboys following you to the closest concert venue. 

5. With Some Leggings and Some Socks

Try as we might, most of us just can’t quit a simple black legging. And apparently, we don’t have to – even when ankle boots are in the rotation. Journalist and tastemaker Sabina Socol gave “weekend chic” in short black rainboots paired with the longtime lounge queen fave, plus casual grey socks. And now, well, I know what I’ll be wearing every Saturday from now until April.

6. With a Sleek Black Taper

Repeat after me: “We will never pair our ankle boots with skinny jeans.” Lovisa Barkman avoided the trap expertly here, by opting instead for a slim, tapered variety over the uncomfortably huggy version we all wore for far too long. Go for a sleek, slim boot in the same colorway to keep the visual lines as long and uninterrupted as our shopping receipts on Black Friday.

7. With a Matching Leather Jacket

‘Fits that slay together stay together. Pair a sleek mahogany ankle boot with a matching leather bomber to give Top Gun chic, and make it a trilogy. Not @leasy_inparis trying to catch Miles Teller’s eye – but if she were, I’d say she’s doing a pretty solid job. (We won’t tell her he’s taken.)

8. Comfy with a Thick Lug Sole

If we know anything when it comes to fashion, it’s that first, last, and everything in between: Comfort. Is. Queen. Pair thick lug sole boots with an oversized sweater and fluffy scarf for textbook cozy, and feel like you never left your bed. *dream life*

Boot Up

We’re happy to report that ankle boots aren’t going anywhere this winter, and neither is your style icon status if you style them correctly. Stick to the cardinal rules (opt for a boot with a higher shaft, rather than one that cuts off below the ankle, and don’t even think about skinny jeans), and you really can’t go wrong. When in doubt, follow our favorite rule of thumb when it comes to iconic style: Channel your inner ‘90s supermodel, and let your imagination run wild. She’ll never lead you astray. 

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