The Dark Shirt

When you think of film noir depictions of characters who wear dark dress shirts with suits, certain disturbing incidents may come to mind—in particular, Richard Widmark as a psychopathic killer, shoving a wheelchair-bound widow down the stairs in Kiss of Death. The look made its way off the screen onto the garb of another unsavory character: “Crazy” Joe Gallo. But we’re here to tell you that—when done right—the dark shirt isn’t crazy at all.

Jack Simpson, who customizes wardrobes for a coterie of refined customers with his Jack Simpson Couture, champions the look, when done with elegance. For him, it’s “a rakish alternative for evening pursuits.” (That is to say, decidedly not rubbing out your rival’s mom). A-listers who have pulled it off include Keanu Reeves (pictured), Jack Nicholson, Samuel L. Jackson, Douglas Fairbanks Jr., Denzel Washington, George Clooney, Brad Pitt and Charlie Watts, the drummer who sported a Savile Row wardrobe.

The key, says Simpson, is contrasting fabrics, which add dimension to ensembles that contain several elements: the shirt, a jacket (alone or as part of a suit), necktie, pocket square and even a vest. He points his customers to chambray and Japanese denim shirts, cashmere ties and tweed jackets. Especially tweeds. He even prescribes the weave for summer wear when smoking under the stars. “Cigars beg for tweed,” he says, pointing out their similarities in appearance. “Look at a stogie and what you see is tweed.”

Part of the charm is the dark shirt’s insouciance. You’re neither cow-towing to the restraints of the white shirt culture, nor making an overt statement out of your casual cool. “I encourage each of my clients to have one glam chic ensemble in their wardrobe,” says Simpson. “His wife will have more than one of these, and he should have at least one.”

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