I Want to Be the Man Who Wore Boxers to Milan Fashion Week


ilan Fashion Week may be over, but its cup of street style runneth over into the eternity that is my imagination. I am personally a street style outfit bookmarking fiend, which is extremely helpful when it comes to maintaining ample style fodder over the course of the season — or at least until fashion month rolls around again. We talk a lot about copying street style outfits on Man Repeller, largely because there is something so immediately gratifying about looking at something another person has already worn and thinking to yourself, Hey, I could wear that too! But also because, in many cases, seeing the way different pieces are paired together in real life on real people helps you see the clothes in your closet in a new light. On that note, I selected five looks from Milan Fashion Week I want to recreate — and yes, one of them prominently features boxer shorts. Keep scrolling and see for yourself.


I don’t know anything about the man who wore literal boxers to Milan Fashion Week except that I want to be him. I like everything about his chosen combination of clothing, which falls under a previously unexplored aesthetic umbrella I’m going to call “Skype Interview Chic” wherein the top half of an outfit is incredibly stylized (see: striped button-down, olive blazer, statement necklace, statement glasses, safari hat) and the bottom half of an outfit is suited for private home activities like sleeping or microwaving a Hot Pocket (see: boxers). I plan on copying the entire ensemble as soon as I purchase a pair of boxers to call my own, but since I can’t see his shoes I’ll have to go rogue on that front. I’m thinking Tevas.


Leave it to Tamu McPherson to recalibrate my conception of what a Naked Dress looks like. Her outfit is a refreshingly updated take on this age-old style phenomenon, which has undergone many iterations since Kate Moss wore a completely sheer slip with nothing underneath except black cotton underwear in 1993. I’m into Tamu’s version for reasons including but not limited to seasonal versatility and multi-occasion practicality, because there’s only so many times of year and so many occasions where you can get away with wearing something totally see-through. Her dress combines the best of both worlds: the inherent sex appeal of a body stocking-esque overlay with the inherent intrigue of a patterned slip, a pink ruffle and cowboy boots, because why not?


As I mentioned, I love day-dreaming (and night-dreaming) about street style looks I want to copy, so I am especially appreciative of outfits like this one that are endlessly captivating and breathlessly simple at the same time. The simpler an outfit is, the easier it is to recreate. Granted, I don’t have this precise suede dress with cutout holes, but I do have one in a similar silhouette, and I definitely have a pair of bootcut white jeans, a delightfully loud canvas tote and plain loafers. In conclusion, I know exactly what I’m going to wear tomorrow.


There are few things I love more than an outfit that speaks in exclamation points, so it’s no wonder I’m drawn to one that combines a wildly striped statement coat with oversized cargo pants, a gingham tube top and — the pièce de résistance — clogs! I don’t have all the components necessary to copy it in its entirety, but I do have cargo pants and I do have clogs, and I do have a closet full of similarly punctuated garments that, when combined, shout my existence into the world at a very high decibel. The only outstanding element I think I  need to acquire are oversize sunglasses circa Mary-Kate and Ashley in the early 2000s (are they coming back???).


I showed this photo of Chloe Hill to Leandra because it features her purple wedges, and she commented that the outfit as a whole was a really nice way to wear lots of color and pattern without looking like a caricature. It struck me that that’s probably why I was so drawn to it in the first place, because as someone who self-identifies as a maximalist, I’m keenly aware of moments when I lean so hard into this identity I lose the very aspects of my personal style that underscore who I actually am instead of underscoring an idea of who I am — if that makes sense? Anyways, I’m very inspired.

Are there any outfits you bookmarked from Milan Fashion Week for copying purposes? Tell me tell me tell me!

Photos by Matthew Sperzel @sperzphoto.

Harling Ross

Harling is a writer and was most recently the Brand Director at Man Repeller.

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