In many ways, the raddest work shirts on the market right now are the polar opposites of your average button-up. Sure, classic poplin or crisp cotton make for fantastic office shirts, but they’re always one loose coffee lid away from a hurried trip to the cleaners. The work shirts you should be wearing as summer winds down—with a tank, a vintage tee, or, hell, a tie—are crafted from far tougher stuff: hefty twill, sturdy canvas, all-American denim. They typically feature a duo of chest pockets to help distinguish them from the rest of your wimpier button-ups, and, true to their name, they genuinely look better the longer and harder you break ’em in.
Mercifully, you don’t have to sling a hammer at your 9-to-5 to appreciate the benefits of an American classic that’s literally designed to withstand the daily grind. If your office skews relaxed, tuck one into khakis anchored by chunky black derbies—and if your office skews really relaxed, lean into the vibe with a pair of sawed-off Dickies and scuffed slip-ons. Whether you nab one from an OG of the genre or opt for a contemporary riff from a small-batch indie name doesn’t really matter: come fall, you’ll be glad you grabbed a daily overachiever that looks just as killer on its own as it does peeking out beneath a waxed canvas jacket.
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