Can Men Wear a Baseball Cap Without Looking Like a Frat Boy? WSJ article

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Yes LIKE APPLE PIE, Paul Rudd movies and surreal Super Bowl commercials, the classic baseball cap is a beloved American institution—and not just for kids. “I’ve realized that in America, they’ve become the modern-day cowboy hat,” said Alex Wilcox, the British co-owner of bespoke clothier and tailoring shop Lord Willy’s in New York. And like the cowboy hat, Mr. Wilcox added, baseball caps connote masculinity, and give men of any age a stylish way to hide. They’re also legitimately fashionable now.

No longer just the province of frat guys and truck drivers, the ball cap has been infiltrating menswear’s more upscale corridors. French luxury brand Louis Vuitton recently sent dark leather ball caps down its runway, paired with elegant outerwear. Gucci and Balenciaga both sell pricey versions. And style icons like Jake Gyllenhaal and Pharrell Williams have made the caps indispensable elements of their wardrobes.

So how to pop one on without looking like you’re heading to a cutthroat beer pong tournament? Consider this scenario: a fitted navy blue ball cap worn with a dark blazer and light linen pants to an outdoor cocktail party—sporty, yet appropriate. Naturally, we’d hesitate to accessorize a formal suit and tie with a cap. “You have to style it with the right pair of jeans, or a cool sneaker, or a cool bomber,” said Todd Snyder, the New York-based designer whose eponymous brand offers sharp ball caps in fabrics like seersucker in collaboration with New Era.

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No FOR JUST ABOUT everything in life, there is a time and a place. And for ball caps, that time and place is the baseball field during a baseball game. Or possibly, that grassy knoll where you used to play ultimate Frisbee back in college. But now that you’re an actual adult with obligations more pressing than bringing a bong to a knoll, retire the cap. “I think if you have a full-time job, and you’re not living in a fraternity house or a dorm room, it’s time to upgrade,” said Kirk Miller of Miller’s Oath, a bespoke menswear shop in New York City. Though Mr. Miller isn’t 100% against ball caps for grown men—he wears one on Saturdays when he coaches his son’s soccer team—he believes they generally should be restricted to their original context, outdoor sporting activities.

As fashion accessories, they don’t work after a certain age, he thinks: “I just feel like you should move beyond that once you’re out of your early 20s.” If you are intent on a hat, Mr. Miller suggests graduating to something more sophisticated. A Panama hat, for instance, or a beautifully made fedora with a grosgrain ribbon, just like your dad might have worn. “I don’t feel like ball caps have a whole lot of personality,” he explained.

When you wear a ball cap as an older man, it also raises the question of what lies beneath. People may assume that you’re hiding bad hair, or sparse hair. “Ball caps are a substitute for laziness,” said Michael Haar, owner of Haar & Co. Barbershop in New York’s West Village. Mr. Miller added that he understands why guys wear them: “Some because they’re losing their hair, some because they didn’t want to brush their hair.” But adopting this quick fix for hair shame is an immature solution, he argues. True gentlemen groom their hair if they have it—and embrace their baldness if they don’t.

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