STYLE EVOLUTION

An Appreciation of Diane Keaton’s Kooky, Suit-Friendly Style, from Annie Hall to The Young Pope

Diane Keaton practically arrived on the scene as a style icon in the ’70s, even before all the ties, hats, and high-waisted pants that her title role in Woody Allen’s Annie Hall required of her in 1977. As it turned out, that was just the beginning: In the last four decades, Keaton has not only made a name for herself for borrowing from the boys and consistently putting her suited partners like Warren Beatty to shame, but also for having an eye for unexpected accessories, from piles of pearls and heels with socks to her personal favorite: a glass of red wine. It’s a style that’ll once again be on fully display for the actress, who just turned 71 this month, thanks to her role as Sister Mary in HBO’s The Young Pope, where she steals the show from Jude Law’s tiny white cap in both a graphic tee that reads “I’m a virgin, but this is an old shirt” and her steady roster of long, flowing nun habits, not so unlike the elegant, obscuring garbs—essentially glorified body bags—she’s also wont to wear on the red carpet. See her best ensembles from over the years, here.

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Diane Keaton and Woody Allen after filming Annie Hall on Madison Avenue, ca. 1977.

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Diane Keaton at the 50th Annual Academy Awards in 1978.

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Warren Beatty and Diane Keaton at the opening night of Richard Avedon’s exhibition “Avedon: Photographs, 1974-1977” at the Metropolitan Museum of Art in 1978.

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Diane Keaton in New York, ca. 1980.

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Diane Keaton at the opening of A Mom’s Life in Hollywood in 1992.

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Diane Keaton at a Los Angeles screening of Fallen Champ: The Untold Story of Mike Tyson in 1992.

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Diane Keaton at the “Cool Comedy—Hot Cuisine” Scleroderma Research Foundation Benefit in 1993.

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Diane Keaton at the 51st Annual Golden Globe Awards in 1994.

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Diane Keaton at a Los Angeles screening of Amelia Earhart: The Final Flight in 1994.

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Diane Keaton at the 52nd Annual Golden Globe Awards in 1995.

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Diane Keaton at New York screening of Unstrung Heroes in 1995.

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Diane Keaton at the Los Angeles premieres of What Women Want in 2000.

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Diane Keaton at the Los Angeles premiere of The Score in 2001.

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Diane Keaton at the 61st Annual Golden Globe Awards, where she won Best Performance by an Actress in a Motion Picture—Musical or Comedy for Something’s Gotta Give, in 2004.

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Diane Keaton at the 54th annual Berlinale International Film Festival screening of Something’s Gotta Give in 2004.

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Diane Keaton at the Los Angeles premiere of The Family Stone in 2005.

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Diane Keaton at the L’Oréal Legends Gala benefiting the Ovarian Cancer Research Fund in New York in 2006.

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Diane Keaton on the street in Soho, New York in 2013.

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Diane Keaton at the L’Oréal Paris’ Women of Worth Awards in 2013.

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Diane Keaton at the Carousel of Hope Ball in Beverly Hills in 2014.

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Diane Keaton at the New York premiere of And So It Goes in 2014.

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Diane Keaton at the L’Oréal Paris’ Ninth Annual Women of Worth Awards in 2014.

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Diane Keaton at the Hammer Museum Gala in Garden sponsored by Bottega Veneta in 2015.

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Diane Keaton at the L’Oréal Paris Women of Worth Celebration in 2016.