What the recent Milan Fashion Week street style says about dressing imperfectly

There was a certain rawness to the street style seen during the Spring/Summer 2027 Milan Fashion Week. Photo: The New York Times

When playing with imperfection and undone-ness, there’s a thin line between intentional and careless.

Just think about the untucked or unbuttoned shirt: Done right, it projects effortlessness and allure. Done wrong, it can look sloppy, lazy or even unprofessional.

At the Spring/Summer 2027 Milan Fashion Week, people flirted with that line in ways that ranged from cautious to daring.

It made sense in a city like Milan, which is practically synonymous with sensuality. Several guests arrived to shows with tops wide open, exposing a maximum amount of cleavage and chest.

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I saw tops that resembled button-downs, but had no buttons, and others with necklines that swooped low to the abs.

A few women sported suit jackets and blazers with nothing underneath. It was a miracle that everyone managed to stay just covered up enough to stay street legal.

Trousers took on that undone look, too. They were worn slouchy and a bit shapeless.

Many were paired with similarly louche unbuttoned shirts – though some people tucked them in with a belt, in an effort to retain a level of sophistication.

Collars got clever, with ruffs and chokers cropping up. Absent these, a shirt simply worn backward was plausible.

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Collections on the runway also seemed to embrace an insouciant spirit.

Jil Sander styled a couple of looks with a layered top that slid off the model’s shoulders. At Marni, carefully constructed looks were made up of garments that might look completely disassociated in one’s closet.

Diesel gave us shamelessly short shorts, while actors made out with each other in the crowd, and Moschino went against the grain, showing a collection largely lacking the quirky touches that the house has long been known for. – ©2026 The New York Times Company

This article originally appeared in The New York Times.