How to Style High Top Sneakers

(And not look like a teenage boy.)
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(And not look like a teenage boy.)

In our latest column, "Ask a Fashionista," you can solicit our strongly held opinions on everything from how to wear a midi skirt without looking like a tree stump to whether a certain retail CEO should go ahead and resign already. Have a question? Email us at ask@fashionista.com.

Q: I own lots of pairs of high top sneakers but don't know how to style them to look flattering with jeans or skirts. Help!  — Allison, Chicago, IL

A: Don't panic. The high top conundrum is real. 

As a person who prefers the high top version of every shoe, from creepers to Nike Dunks, I've struggled with styling my kicks for decades – and I'm going to share everything I've learned. 

The first step to figuring out how to wear the tricky sneakers is identifying the type of high tops you want to wear. I break them into two categories: thin and thick. A thin high top is something like a pair of Chuck Taylor All Stars, a shoe that is made of a light fabric that, when tied to the top, rests snugly against the leg. An example of a thick version would be a Nike Air Force 1 that is wide at the ankle and has more bulk. 

OK, let's start with the harder of the two: the thin high top. 

The issue with a thin high sneaker is that when laced all the way to the top tightly it can make one's ankles look awkward and small – especially when paired with skinny jeans or tights. My first trick is to never, ever lace the kicks to the top loop, and instead tie them in the middle loosely so that the sneaker tops aren't tight against the ankle. The second trick is to wear pants with your high tops that are wide at the bottom or allow for a peek of skin to pop out between the pants and shoes – this will keep your body proportions feeling right.

The picture of Kati Nescher above is a good reference for a casual look, while I also love this just rolling the bottoms of jeans to create volume to offset the sneakers. For the most part, I'd say steer clear of dresses or skirts with thin high tops – it's maybe a little too Avril Lavigne at the prom? – but to each her own. 

Check out these high tops for some thin sneaker inspiration.

And now for the thick high top ....

When it comes to a chunky sneakers, you can go down one of two roads. The first is to pair it with bare legs and a miniskirt, like Ashley Madekwe did above. Because the shoe has weight, it can stand on its own, and usually looks best without baggy pants or tights competing with it. 

The other option, illustrated below, is to pair a chunky sneaker with a skinny jean tucked into the sneaker. It's the pants equivalent of going bare-legged, leaving the kicks to stand alone as the accent of the lower half of your outfit. 

Try it out with some of my favorite high tops in the gallery. 

Homepage photo: Timur Emek/Getty Images