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What Your Shoe Says About You

  1. Shoe Complete Me
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    Shoe Complete Me

    There are at least two fast ways to judge a man: by his books and by his shoes. "It’s the classic stereotype," says stylist, consultant, and former Saks Fifth Avenue menswear director Michael Macko. Unlike what a man reads on the train, his footwear is on display throughout the day—from board meeting to bathroom stall. And those shoes are always saying something, especially at the office, where these days "we’re seeing all kinds of great shoes," says Kevin Harter, director of menswear at Bloomingdale’s. Men now are able to get away with wearing a much greater variety of shoes during the workday, in materials ranging from canvas to suede—even alligator—and in styles from strap closures to slip-ons. Color, Harter adds, is one of the moment’s big trends. But before you swap out your black oxfords for a pair of yellow suede loafers, stop and consider what that might communicate about you. Better yet, have our panel of experts do it for you. In addition to Macko and Harter, Bloomberg Businessweek tapped William White, founder of the high-end shoe brand Di Bianco, and Paul Grangaard, chief executive of Wisconsin shoe manufacturer Allen Edmonds, to offer insight into your sole.
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  2. The Elegant Executive
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    The Elegant Executive

    Bruno Magli, $425
    Bloomingdale’s, 800-232-1854

    Executives at the top of the food chain gravitate toward exotic shoe materials such as alligator skin. "He’s into sports cars, private jets, and cigars," Macko says. While five-figure shoes won’t go out of style, White says if they’re red or blue, they’re probably the spoils of "a good weekend in Vegas."
    Ward Sutton/Davies and Starr
  3. The Sharp Dresser
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    The Sharp Dresser

    Allen Edmonds, $295
    Bloomingdale’s

    "He's not cookie-cutter," Harter says of the guy who wears a wingtip brogue with decorative perforations. "He's a gentleman and likes the idea of going to lunch in a three-piece suit." Even if it's a skinny suit with a skinny tie. "It's a fashion look," Macko adds. "He's willing to take risks, but ones you usually win."
    Ward Sutton/Davies and Starr
  4. Mr. Ubiquitous
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    Mr. Ubiquitous

    Ferragamo, $460
    Bloomingdale’s

    The universal penny loafer—alongside its frilly cousin, the tassel loafer—is the default shoe for corporate casual, whether you’re "a khaki-wearing dot-com CEO or a lawyer who doesn’t have to be in court," Macko says. Though Harter points out, "More hip guys are wearing these with suits."
  5. The Free Spirit
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    The Free Spirit

    Jack Purcell, $60
    Bloomingdale’s

    A canvas sneaker conveys simplicity. "He wants to be comfortable and unrestrained," says White. "He doesn’t care what other people think." These might be the same shoes he wears on weekends, on dates, or to the gym—although, "he’s not necessarily an athletic type," Harter says.
    Ward Sutton/Davies and Starr
  6. The Dudeademic
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    The Dudeademic

    Mark McNairy, $350
    markmcnairy.com

    The suede chukka is both casual and dressy, ­purposeful and bohemian. "He travels, maybe has a little country in him—or he could be an academic," White theorizes. Either way, he’s versatile. Notes Macko: "He’s a little more cerebral and creative. He has a Nerf basketball hoop on his garbage can."
    Ward Sutton/Davies and Starr
  7. The Uninhibited Aristocrat
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    The Uninhibited Aristocrat

    Regain, $550
    Bloomingdale’s

    A monk-strap oxford is a "jaunty" alternative to the lace-up, notes White. A double-monk in blue suede, however, is "a shoe that you need a valet for," Macko says. Worn with some restraint, it conveys sophistication. At its fussy extreme, he argues, it's decidedly "more femme than butch."
    Ward Sutton/Davies and Starr
  8. "That Guy"
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    "That Guy"

    Di Bianco, $6,000
    scarpedibianco.com

    Executives at the top of the food chain gravitate toward exotic shoe materials such as alligator skin. "He's into sports cars, private jets, and cigars," Macko says. While five-figure shoes won't go out of style, White says if they're red or blue, they're probably the spoils of "a good weekend in Vegas."
    Ward Sutton/Davies and Starr
  9. The Rich Old Man (R.O.M.)
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    The Rich Old Man (R.O.M.)

    Tod’s, $425
    tods.com

    The suede driving moccasin—preferably by Tod’s—is the ultimate rich man's leisure shoe. "He's relaxed and doesn't want to wear socks," Harter says. White adds: "His wife or girlfriend spends time looking through the better fashion magazines." Macko: "This shoe definitely says, 'I have a country house.' " Or five.
    Ward Sutton/Davies and Starr
  10. The Drifter
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    The Drifter

    Sperry ­Top-Sider, $85
    sperrytopsider.com

    Somehow, the boat shoe has veered mainstream. Sperry's version has even been co-opted by hipsters. "He's definitely casual," Macko says. "He hasn't put any thought into his wardrobe," White argues. "Assuming he's not a sailor or in high school or college, I think it's a guy who needs a girlfriend."
    Ward Sutton/Davies and Starr
  11. The Starchitect
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    The Starchitect

    Bally, $475
    Bloomingdale’s

    Even if the hotshot who wears Chelsea boots is not an actual rock star, Harter says, "he feels like one." Macko, however, detects a self-disciplined streak in this mod-influenced style. "He has a design aesthetic, but he's very structured." White: "He's a little more cultured. He wears black turtlenecks."
    Ward Sutton/Davies and Starr