"So the flannel shirt deal—is that a nod to the crispy Seattle weather, or are you just trying to stay warm in front of the refrigerator?" Most movie buffs and fashion fans, of course, can instantly ID this line from Clueless, in which Cher Horowitz pokes fun at stepbrother Josh’s lumberjack-turned-hipster style sense. But while the humble plaid button-up may have carried grungy connotations back in the ’90s, it’s undoubtedly one of this season’s must-have buys. In fact, it’s near-impossible to scroll through our favorite style blogs or flip through a magazine without spotting a celebrity or model in a checked flannel these days.
Despite its obvious popularity, however, the plaid shirt can be surprisingly tricky to style. But fear not—I’m here to help you out. Click through above to see one of my favorite plaid tops, Rails’ Kendra button-up ($128, railsclothing.com), styled into a whopping 10 different looks—some work-appropriate, others tailor-made for the weekend.