As a good New Yorker, I’m a head-down, earbuds-in type when it comes to my morning subway commute. But early last week I found myself ogling—in the face of propriety, and against my better judgment—at a sharp-looking fellow straphanger. “Against my better judgment” because the guy looked like he could’ve kicked my ass the rest of the way to Herald Square—a not-to-be-messed-with quality due in no small part, I submit, to the item unapologetically placed atop his head: a black beret. I hadn’t seen one of those since Cloak & Dagger (and no, I won’t be making the case for Dabney Coleman as a style icon), and I’ll be honest: I’d always thought of berets as relics, the bygone emblems of midcentury French schoolboys, Cubist painters, and Latin American revolutionaries. But this guy looked, well, amazing—and very 21st-century. Then came Friday’s Jake Davis/Gilt MAN event at the SoHo Apple Store, where I spotted not one but two of New York City’s most stylish young gentlemen rocking wool felt berets—Joshua Kissi of Street Etiquette, above, and James Jean. So hell, I’m just gonna go ahead and call this “a thing”—and a good one, at that. I’ve done a little archival research to back up that claim, and throw some light on the uber-stylish lineage of winter’s most righteous piece of alternative headgear.