Shorts are a constant topic of conversation here at GQ HQ. Should you wear them at night or to the office? Should you make them your whole personality? Should you wear them…at all? For particularly particular dressers, half-pants present the ultimate warm-weather paradox. Damned if you do (and risk looking sloppy), damned if you don’t (and end up drenched in sweat).

The solution here, of course, is to go forth and wear shorts boldly and with true panache. Take a cue from shorts expert Paul Mescal and opts for some high-fashion cotton boxer shorts, or go the more languorous route in leather basketball shorts, a pleated midi skirt, or some below-the-knee waders. Below, photographer Cris Fragkou braved the balmy Milanese temps to document all the expert-level shorts and skirts ensembles on display at the latest men’s fashion shows.

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