How to Wear the #1 Boot Trend of Fall

leandra medine boots man repeller

Imagine the year is 2016. It is mid-fall and we are sitting on a couch covered in egg yolks while drinking peach schnapps, discussing the difference between people who jiggle the handles of locked doors and those who knock. We’re probably both wearing slightly cropped flare leg jeans. They’re either Michelin-grade vintage Levi’s scouted from the depths of a pile at a store in a remote town somewhere in the middle of America. With our jeans, I can only imagine we’re wearing ankle boots. Yours are black, mine are silver, and just as you are about to wax poetic on the redeeming qualities of an insensitive door jiggler, I ask you the most critical question I will probably posit in this lifetime.

Will knee-high boots ever make a comeback?

Surely, I will argue, they won’t. They can’t! They require that you wear skinny jeans, that you cut your legs in half with their harsh, stiff shaft. They don’t look right with a long coat—they conceal the bottom of your pants and it is suffocating. When you wear them with a skirt, if it’s long, you kind of look like a grade-school teacher. When you wear them with a skirt, if it’s short, you run the risk of getting fired from your job. And say you don’t wear skinny jeans—say you choose a pair of tapered trousers. Well, that doesn’t work, either. Now you’ve dressed as a relic of an era bygone and I don’t know about you, but when people look at pictures of me in The Future, I want them to know, based solely on what I’m wearing, which year it was when the picture was taken. Call me modern, call me old-fashioned, call me postmodern if you’re conceptual!

But lo and behold, here I am, in the year 2019, absolutely, positively, capital-C-Certain that there is no way around The Next Great Boot Trend and from here on out its knee-high or no-high. Whatever that means. But make no mistake, for as convicted as I might seem in the following three photos, for as severely as my rhetoric may influence your opinion on knee-high boots, I am well aware that I, too, am under an influence. That I used to hate knee-high boots and now I don’t. Something has been steaming in the zeitgeist’s Yeti thermos and g-dangit, I’m just about ready to take a giant gulp.

The thing is: I’m still not completely sure how I’m going to wear them. Just that I want to—that no other winter footwear feels quite as fresh. So here’s a three-part stab at becoming a knee-high boots person, written as if Friends episode titles:

The One With the Sweatpants

Antolina boots, Celine shirt, Toteme sweater, Leandra Medine x Mango sweatpants, Ray-Ban sunglassesAntolina boots, Celine shirt, Toteme sweater, Leandra Medine x Mango sweatpants, Ray-Ban sunglasses

Could I be wearing pants that are any more comfortable? They kind of serve the same purpose as a pair of tapered trousers but read somewhat more modern because in 2019 athleisure is just leisure and leisure is a synonym for existing. I have them styled with a black wool sweater that is slightly asymmetric at the hem, and a striped shirt with a curly collar. These boots are from a brand called Antolina and I’m pretty sure this is the kind of outfit I’d wear to work on a Friday, to run errands on a Saturday, to see a movie on a Sunday, to fly to domestically on business on a Wednesday.

The One With the Big-Ass Tote

I know, I know, it’s missing a collarless coat, but on the bright side, the bag is enough to crawl into and cry! I don’t think I actually deserve credit for styling this look because it seems like part-4 in a series called How to Reapproximate New Celine, by Leandra Medine Cohen, avid admirer of Polo Ralph Lauren denim shirts, sporadic identifier of looks-4-less (the boots are Mango!). I don’t know if you remember Kors by Michael Kors, but I spent the greater part of the very early 2000’s wearing a pair that looked kind of like these. Here’s a picture. I’d wear this to a Canadian tuxedo convention, or out for dinner during the week, to work because the dress code at my office is null, after a workout, or before a gala—because my tote is huge and I can basically change into or out of it at my (here’s that word again) leisure.

The One With Two Blazers

The first two looks were pretty much styled in advance but the third look, staring you slackjawed above, was a placeholder. Would I wear a long skirt? A mid-length dress? Shorts? A mini skirt? WOOL UNDERWEAR? In the end, the outfit picked me, really. I layered two blazers on top of each other and paired them with a mini skirt by Stella McCartney, which I bought when I was in London 4 years ago for Fashion Week. I bring this up only because I have never shared the following: When I was getting de-tax on the skirt at the airport, the person stamping my paperwork shamed me for spending however many pounds on such a small skirt. The shame has been too much to release, but you know what Brené Brown says, the only way to expel it is to call it out, so I’ll never get rid of the skirt based on that accord alone.

And now! I turn the mic, the selfie cam, the back end of WordPress over to you: are you going to wear knee-high boots? Have I sold you? Were you already sold? Do you really believe that a person can shake their sillies out? SOS (Send One-legged Selfie). And here are some boot options priced from $79 to $995:

Photos by Franey Miller.

Leandra M. Cohen

Leandra M. Cohen is the founder of Man Repeller.

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