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The men and women who rise to the top of the business world have strong and distinctive personalities. The same words can often be applied to their fashion sense. Love them or hate them, the trademark turtlenecks, baseball hats, and...interesting hairstyles project the personalities of their wearers.
by Sara Clemence
Larry Ellison
Though the Oracle C.E.O. sometimes appears in Italian-tailored suits, Ellison’s trademark look is a T-shirt (usually black) or cashmere turtleneck under a sport jacket. For the billionaire entrepreneur/yacht racer/jet pilot, it’s a power version of casual Silicon Valley style. And, oddly, it carries echoes of Miami Vice.
Oprah Winfrey
The media mogul’s signature look starts high up—with shawl collars, portrait collars, broad lapels, and cowlnecks that keep the focus around her famous face. The rest of her look is elegant and monochromatic—but not monotonous. Oprah goes with distinctive colors, including ice blue, dove gray, and cherry red.
Steve Jobs
Do you need to dress the same to think different? Steve Jobs’ look is unwavering: blue jeans, black mock turtleneck (tucked in), and sneakers. His feet made news in 2006 when Jobs appeared to be shifting footwear allegiance from New Balance to Nike, but he quickly went back to his old ways. Whew.
Andrea Jung
Some might consider her signature orange-red lipstick garish, but if the C.E.O. of Avon can’t get away with it, who can?
Martha Stewart
Stewart’s dress is Connecticut casual—she’s often in button-down shirts and cardigans—but always in control. Though she prefers Christian Louboutin shoes, she admitted on her blog that “I am not a fan of the signature red soles.” So she has a staffer paint them with a black Sharpie.
Warren Buffett
“I buy expensive suits,” the Oracle of Omaha has said. “They just look cheap on me.” Good thing he’s better known for his oversize, square-frame eyeglasses. Do they make him look like more of a visionary—or more of a grandfather?
Russell Simmons
The hip-hop pioneer was instrumental in bringing street cred to Tommy Hilfiger, and he may be the best advertisement for the urban-preppy style sold by his Phat Farm brand. In sweater vests, polo shirts, and oversize baseball caps, he manages to make square look cool.
Donald Trump
The dark suits and silk ties say money. After all this time, no one is quite sure what the hair says.
Meg Whitman
While C.E.O. of eBay, Whitman took it from startup to colossus. She didn’t apply such transformative or risk-taking powers to her look, which is about as conservative as it comes—black suit, collared shirt, maybe a scarf tucked along the lapel.
Angelo Mozilo
While running Countrywide, he wore white collars and chalk-stripe suits with gangster-like aplomb. Somehow that
seems less amusing now.
Indra Nooyi
The Pepsi C.E.O.’s boardroom attire isn’t especially notable, but the silk saris she occasionally dons are.
Mark Zuckerberg
The 24-year-old chief executive of Facebook brought dorm-room style to the C-suite with hoodies, faded T-shirts, and Adidas flip-flops. Not that that’s a good thing.
Mary-Kate Olsen
She’s known as an actress rather than an executive, but the 22-year-old controls a billion-dollar business with her twin. Ironically, her bag-lady style—layers of grungy-looking sweaters, ankle-length skirts, lank hair—was copied by untold legions of young women.
Chad Hurley
Still in his twenties, the YouTube C.E.O. manages to look grown-up but not uptight in jeans, open-collared white shirts, sport jackets, and longish hair.
Sole Searching
