The Most Stylish Women Ever

On the cusp of his label's 25th anniversary, we asked Tommy Hilfiger to weigh in on the ladies who've inspired him over and over.

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"Jackie Kennedy is the classic American style icon."

Photo Credit: Hulton Archive/Getty Images

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"Marilyn Monroe is famous for the billowing-white-dress moment, but for me it was her more casual sexiness that I remember: a pair of jeans and a white oxford shirt."

Photo Credit: Eve Arnold/Magnum

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"Not only is Beyoncé a trendsetter with her effortless look, but she is a true role model for so many young women."

Photo Credit: Splash News

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"Ali MacGraw's unconventional simplicity in The Getaway, with Steve McQueen, was fantastic. She has a special way of drawing you in."

Photo Credit: First Artists/Courtesy of Neal Peters Collection

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"Grace Kelly is the princess of class. She is timeless and the ultimate definition of charm."

Photo Credit: Howell Conant/Bob Adelman Books

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Our Picks From the Icon Collection

Offering up 25 flawlessly rendered pieces, this entire limited-edition mini line telegraphs the deeply American aesthetic that Hilfiger has made his own.

This shawl-collar fisherman's sweater is so Cape Cod–at-its-chicest.
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A brilliant—and insanely cool—update on the cowboy boot.
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Crisp and oversize but tailored exactly where it counts.
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Perfectly slouchy and worn-in, these already look like your best-loved jeans.

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