As evolving office dress standards have made the suit and tie superfluous in many workplaces, the button-down shirt has become a man's defining fashion statement. "The shirt," says Eric Jennings, men's fashion director at Saks Fifth Avenue, "is where you can express yourself."

With all those men expressing themselves, discerning shirt signals from shirt noise, as it were, has never been more difficult. Particularly because "We're at a moment in the fashion cycle where sport and dress, and business and casual, are colliding," says Jeff Blee, divisional merchandising manager for men's accessories at Brooks Brothers. This means shirts that were once reserved for after work are now becoming commonplace from 9 to 5.

Historically, collars--from the British-inspired spread collar to the casual American button-down--have separated the managers from the managed. These days, though, an array of collar styles, colors, fabrics, weaves, cuffs, and patterns are flooding the workplace. Each shirt communicates something different--but what? Bloomberg Businessweek posed that question to a handful of experts, including Blee; Jennings; Sam Spector, a prominent New York City-based stylist; John Minahan, chief executive officer and president of shirtmaker Gitman Bros; and Brett Fahlgren, an established men's style consultant. Next time you get dressed for work, you'll know what statement you're making.
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As evolving office dress standards have made the suit and tie superfluous in many workplaces, the button-down shirt has become a man's defining fashion statement. "The shirt," says Eric Jennings, men's fashion director at Saks Fifth Avenue, "is where you can express yourself."

With all those men expressing themselves, discerning shirt signals from shirt noise, as it were, has never been more difficult. Particularly because "We're at a moment in the fashion cycle where sport and dress, and business and casual, are colliding," says Jeff Blee, divisional merchandising manager for men's accessories at Brooks Brothers. This means shirts that were once reserved for after work are now becoming commonplace from 9 to 5.

Historically, collars--from the British-inspired spread collar to the casual American button-down--have separated the managers from the managed. These days, though, an array of collar styles, colors, fabrics, weaves, cuffs, and patterns are flooding the workplace. Each shirt communicates something different--but what? Bloomberg Businessweek posed that question to a handful of experts, including Blee; Jennings; Sam Spector, a prominent New York City-based stylist; John Minahan, chief executive officer and president of shirtmaker Gitman Bros; and Brett Fahlgren, an established men's style consultant. Next time you get dressed for work, you'll know what statement you're making.
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What Your Shirt Says About You

Our Collars Ourselves
Our Collars Ourselves
As evolving office dress standards have made the suit and tie superfluous in many workplaces, the button-down shirt has become a man's defining fashion statement. "The shirt," says Eric Jennings, men's fashion director at Saks Fifth Avenue, "is where you can express yourself."

With all those men expressing themselves, discerning shirt signals from shirt noise, as it were, has never been more difficult. Particularly because "We're at a moment in the fashion cycle where sport and dress, and business and casual, are colliding," says Jeff Blee, divisional merchandising manager for men's accessories at Brooks Brothers. This means shirts that were once reserved for after work are now becoming commonplace from 9 to 5.

Historically, collars--from the British-inspired spread collar to the casual American button-down--have separated the managers from the managed. These days, though, an array of collar styles, colors, fabrics, weaves, cuffs, and patterns are flooding the workplace. Each shirt communicates something different--but what? Bloomberg Businessweek posed that question to a handful of experts, including Blee; Jennings; Sam Spector, a prominent New York City-based stylist; John Minahan, chief executive officer and president of shirtmaker Gitman Bros; and Brett Fahlgren, an established men's style consultant. Next time you get dressed for work, you'll know what statement you're making.
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The Traditionalist
The Traditionalist
Brooks Brothers, $79.50

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.
Neil Swaab/Nick Ferrari for Bloomberg Businessweek
The Loud-Shirt Guy
The Loud-Shirt Guy
Ermenegildo Zegna, $325.00; from Saks Fifth Avenue

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."
Neil Swaab/Nick Ferrari for Bloomberg Businessweek
Fashionisto
Fashionisto
Billy Reid, $195.00

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."
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The Dweeb Savant
The Dweeb Savant
Seize sur Vingt, $200.00

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.
Neil Swaab/Nick Ferrari for Bloomberg Businessweek
The-Dressed-By-Wife-Guy
The-Dressed-By-Wife-Guy
Brooks Brothers, $79.50

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."
Neil Swaab/Nick Ferrari for Bloomberg Businessweek
The Gekko
The Gekko
Ralph Lauren Purple Label, $450.00

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.
Neil Swaab/Nick Ferrari for Bloomberg Businessweek
The Overachiever
The Overachiever
Guy Rover, $265.00; from Barney's New York

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."
Neil Swaab/Nick Ferrari for Bloomberg Businessweek
The Linen-Loving Playboy
The Linen-Loving Playboy
Saks Fifth Avenue Men's Collection, $135.00

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."
Neil Swaab/Nick Ferrari for Bloomberg Businessweek
The Urban Lumberjack
The Urban Lumberjack
Ralph Lauren Purple Label, $450.00

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."
Neil Swaab/Nick Ferrari for Bloomberg Businessweek
The C-Suite Sartorialist
The C-Suite Sartorialist
Thomas Pink, $185.00

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.
Neil Swaab/Nick Ferrari for Bloomberg Businessweek