The pinpoint oxford button-down has no prejudices. It’s for everyone, from prep-school kids to Warren Buffett. Its wearer is “the sort of guy who doesn’t want to stand out in a crowd,” says Blee. Leaving collar points unbuttoned, however, makes a “devil-may-care statement,” Minahan notes.
The Loud-Shirt Guy
The associate wearing a party shirt to the morning meeting isn’t sending the strongest work vibe. “It’s very What-Happens-in-Vegas,” says Spector, who recommends pairing this type of shirt with a suit. In the worst-case scenario, Fahlgren notes, “He’s wearing it hanging over a bedazzled jeans pocket.”
Slim-cut shirts with vintage elements like smaller collars are for younger men who fancy themselves au courant, especially when paired with a skinny suit and tie. “He’s a natty dresser and probably knows every actor on Mad Men,” Minahan says. Adds Fahlgren: “He can make you a Southside Fizz.”
The Dweeb Savant
Fitted check shirts are part of the uniform for many of today’s upwardly mobile workers. “He’s image-conscious and probably in a business where he understands modern media,” Minahan says. “He’s a tactician–even if his shirt colors aren’t always on-trend,” Fahlgren notes.
Favored by middle-management types on the go, the non-iron shirt is more about ease than style. “I think of the guy in the airport with a computer bag over one shoulder,” says Minahan. Adds Fahlgren: “He’s practical and professional–there’s a good chance his wife buys his clothes for him.”
Popularized by Gordon Gekko, the dandyish contrast-collar shirt requires an ego to back it up. “It’s a power broker look,” Jennings says. Although hip designers have been tweaking this bull-market classic, the usual wearer is still an “older banker or a corporate lawyer,” Minahan says.
A large portion of the American workforce is answering to a thirtysomething in a gingham shirt. “It’s really popular right now,” Spector says. “The gingham guy is versatile–he’s cool, maybe he’s a dad,” Fahlgren says. “Either way, he’s comfortable with who he is.”
The Linen-Loving Playboy
Defying common sense, some men wear linen shirts all year. “It’s way too casual for work,” Spector says. Worn seasonally with a summer-fabric suit, though, the well-tailored version can convey Mediterranean savoir faire. However, Minahan says, “Most men don’t dare to do it.”
The Urban Lumberjack
Not yet entirely welcome in the workplace, the flannel shirt conveys a persona that’s part Paul Bunyan and part Polo Ralph Lauren. The shirt signals “a journeyman,” says Fahlgren. “Whether or not he rides a mountain bike or goes to the farmer’s market, he’s looking for something authentic.”
The C-Suite Sartorialist
A crisp, expensive, and perhaps monogrammed white or blue dress shirt with modern spread collar is the standard frontispiece of the guy in charge. “He’s that much richer and more elegant,” Blee says. French cuffs allow more flamboyant honchos to “show off some executive bling,” Minahan notes.
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