A Denim Work Shirt

Rugged, masculine, and eminently affordable, it’s one item of clothing that cowboys, playboys, and backtalking prisoners can all agree on. It also looks equally sharp with khakis and a nicely tailored suit. In fact, the only thing a denim shirt doesn’t look good with is, well, jeans.

Illustration: Mickey DuzyjOn a men’s fashion website I used to edit, we had a recurring feature where we asked various tastemakers (yeah, I hate the word, too) to name their favorite items. Inevitably there came a day when we reached out to Lapo Elkann, the Italian automotive heir who more than any of his peers seems determined to keep the word “dashing” from becoming obsolete. What was the no. 1 pick on Elkann’s list of sartorial must-haves? One of the tailored Caraceni suits he famously inherited from his grandfather Gianni Agnelli, perhaps?  Or the futuristic sunglasses he carves out of carbon fiber for his company Italia Independent? No, it was a Wrangler denim shirt, wardrobe staple of cowboys and playboys alike.

Start investigating the origins of denim and you will quickly find yourself mired in a murky, arcane field of study that can take you from the Wild West to 16th Century Genoa, Italy, without providing any definitive answers. For our purposes, though, we can trace the classic work shirt’s current popularity to 1967. That was the year Warner Brothers released Cool Hand Luke, the film in which Paul Newman proved that going to jail doesn’t mean having to sacrifice your personal style, not as long as your personal style encompasses rugged shirts in a shade of faded blue that perfectly matches your eyes. (Prison’s dietary restrictions, on the other hand, could be more of a hurdle.) Newman and other anti-establishment figures of sixties and seventies cinema (see Nicholson, Jack, Five Easy Pieces) would cause subsequent generations of hipsters from Tokyo to London to spend hours scouring vintage stores in search of just the right western-style shirt. It’s surely no coincidence that Ralph Lauren, Mr. RRL himself, also founded his company in 1967.

These days, of course, every designer, from high end to high street, offers a variation on the denim work shirt. A few guidelines: Choose one that is as well tailored as your favorite dress shirt; unless your daily working environment involves horses and rope tricks, you may want to take long look in the mirror and ask yourself if you’re man enough for flap pockets, pearl snaps, or any other overt Western details (in the case of Wrangler-loving Mr. Elkann, the answer was an emphatic si); and assuming you’re not auditioning at the Grand Ole Opry, don’t pair with jeans but with a suit, Caraceni or otherwise.

Dirk Standen is editor in chief of He also happens to be a fan of wingtips.

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