I’ll never forget the first time I wore a skirt. It was back in September, and I had just seen the Peter Do runway show during New York Fashion Week, which featured pleated knee skirts styled over dress pants. Feeling saucy, I decided to test it out for myself on a trip to my local Starbucks. My ensemble consisted of a black tee, black pleated skirt that I bought secondhand, and black dress pants worn underneath. “Okayyy, skirt,” my favorite barista exclaimed as soon as I strolled in.
I’ve always seen skirts as a genderless piece; As an Ojibwe person, I grew up often seeing men wear skirts at our annual summer powwows. But a fear of judgment and ridicule has always held me back from taking the plunge in public. Walking home with my grande iced coffee in hand, I was pleased to find that nobody even batted an eyelash. It was surprising, though refreshing, that nobody cared about my foray into skirts. (It helps that stars like Lil Nas X, Brad Pitt, Odell Beckham Jr., and Conan Gray have all been wearing them out, too.)
Sure, New Yorkers are largely unfazed in general, but that first successful attempt at skirt dressing has given me the confidence to incorporate even more into my wardrobe. And now, I can’t stop buying them. My growing skirt collection may have something to do with the market being—for once—filled with men’s options. While one could easily shop a women’s skirt, sizing is not always easy to figure out; I’ve attempted to buy some in the largest women’s sizes, only for them to barely fit over my knees. Instead, more and more retailers are finally stocking skirts in dedicated men’s sizes—meaning I no longer have to guess or hope it will fit.
The pleated Thom Browne skirts and sleek leather Rick Owens skirts on Ssense, for instance, now go from a size 28 to 40 waist. I’ve also been eyeing printed styles from Chopova Lowena and Liberal Youth Ministry, both of which go from small to XL. While this range is not as size-diverse as it could be, skirts in men’s-specific sizes is a step forward. My most recent skirt acquisition, in addition to my classic gray Thom Browne, is a black, asymmetrical Airei skirt with frayed edging. I’ve been enjoying pairing with my chunkier knits, like my new checkered Zankov sweater.
In experimenting with these skirt styles, I’ve realized just how easy and foolproof they are to wear. There’s really nothing to it: A black or gray skirt can be paired with just about anything, from knits to simple button-up shirts. Think of them like jeans—just a little more fashion-forward. They look especially good with a chunky boot or loafer.
All this is to say: Gents, if you’ve ever been skirt-curious, now’s the time to buy one. You have both size and silhouette options now, and it’s a no-brainer to style them.
Tempted? Shop six stylish options below.
