Somewhere along the way the plaid shirt got a bad rap. With each appearance on “Do’s and Don’ts” or “Blue States Lose,” the look became—like PBR, kickball, and bands with the word Bear in their name—synonymous with mid-aughts hipsterdom (and then late-mid-aughts hipster bashing). This is a shame, because—setting aside the infinite wormholes that make up the filial-based history of tartans—the plaid shirt occupies a signature place in American history. It bridges the blue-collar world and the artists who fetishize it. Let’s go back to 1954 and Elia Kazan’s On the Waterfront. Suave mob lawyer Charley Malloy (portrayed by Rod Steiger) attempts, at gunpoint, to persuade his ex-pugilist brother Terry Malloy (played by Marlon Brando) to keep quiet and abandon his conscience. Brando, a stalwart of blue-collar solidarity against the pungent corruption of power, refuses. And he does so in a zip-up buffalo plaid shacket (that’s “shirt/jacket,” for the uninitiated)—the plaid serving as the armor against the silk-suited, fedora-sporting powers that be.
Around the same time, the mashup of high ideals and working-man style framed the writings and aesthetic of the Beats. Jack Kerouac regularly donned plaid shirts (along with generous amounts of blue-collar chambray) in throwing his lot in with the hobos, factory workers, and characters on the margins of ‘50s American suburbia. By the time Dr. Dre and Kurt Cobain threw on plaid flannel in the early ‘90s—the former neatly pressed and buttoned up, the latter open and, well, grungy—it wasn’t the quite overt political statement of thirty years prior. And by the time Dre started making Dr. Pepper commercials, the plaid shirt had been safely rinsed of any and all political and social connotations whatsoever.
But whether you want to obsess over the backstory of an American classic or just want to look good (or, more likely, both), you need one. A few guidelines: It can be any fabric. A cotton broadcloth version with a button-down collar leans preppy, but doesn’t scream it. A buffalo plaid shacket will go great with your Gorillas, Wolverines, or Red Wings. And every man needs one or two tartan flannels in his arsenal. Whichever direction you lean, one piece of advice: Keep the Brando impressions to a minimum.