How to Wear Knee-High Boots If You Hate Knee-High Boots

Ten years ago, knee-high boots were so popular you just called them “boots.” They were everywhere, and I hated that, perhaps because I’d developed an impossible-to-explain insecurity about my perfectly-fine calves, and therefore didn’t participate, or maybe because I had an aversion toward their preppy/equestrian aesthetic. Either way, when ankle boots, which I deemed more “city,” finally entered my purview, I was relieved. And when they appeared to replace 90% of tall boots around me within a few years, I was gratified.

Unfortunately, that last 10% persisted a decade on, and my bitterness deepened (a resentment I blamed solely on the boots, not the women who wore them; I loved the women!). But when I started getting sick of my ankle boots some time in 2016, I was shaking in them, so to speak. What could be next? I set my sights on lace-up boots and high top sneakers — anything to ignore the whispers of renewed affection for knee-high boots I heard from the lips of my beloved colleagues (not to mention the runways).

But at a certain point, it became impossible to deny: knee-high boots were back. And probably would be for a while. So, in anticipation of them infiltrating my New York and internet horizon, and to conquer my Pavlovian-like shudder when I see them, I enlisted the help of our Fashion Editor, Harling, who may be the biggest tall boot fan of them all. When I see her wear them, I feel my hateful grasp loosen…but still, I couldn’t begin to imagine them on myself. Below, she found three ways to help me do that, and offered some styling tips, too.

Wear them with a midi skirt

Harling: “I’m a big fan of knee-high boots and wear them with some frequency. Right now, my favorite way to do so is with midi-length skirts and dresses, which is why two of the looks I proposed for Haley incorporate that pairing. That’s my main tip for wearing knee-high boots: Try a midi-length skirt or dress with them. I think it’s less expected than mini-length and also a less abrupt transition if you’re new to the knee-high boot rodeo.”

Find a pair that speaks to you

“If you’re not a knee-high boots person because you don’t identify with their preppy/equestrian connotations, consider a color or pattern or style of knee-high boot that speaks to your personal proclivities, be it purple faux-snakeskin, per above, or slouchy suede with a slight heel. I firmly believe there’s a knee-high boot for everyone.”

Embrace THE LOOK

“The third outfit came about as a result of Haley’s request that I use pants in one of the looks. In the post-skinny jeans era, I’d never really considered wearing pants with knee-high boots because of the baggy knee factor, but Haley reminded me that princess Diana styled herself in this manner on many occasions and not only made it work but made it look EXTREMELY COOL.

So I called in a pair of trousers from Rachel Comey. My advice for styling pants with knee-high boots is to embrace the inevitable billowing. Pretend you’re on the English countryside, or in this case, a Southwestern version of that fantasy courtesy of the oversized jacquard sweater and cowboy-esque boots…”

I never would have put these outfits together! I liked them all, especially the first one, which made me feel like Harling’s evil twin. Now I’m eager to see them in a more boyish/Brooklyn context, too: maybe black leather boots with high-waist vintage Levi’s, a hooded sweatshirt and a blazer? I don’t know if that would work, but the fact that I’m even thinking it feels like personal boot growth.

Photos by Edith Young.

Haley Nahman

Haley Nahman

Haley Nahman is the Features Director at Man Repeller.

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