Hugh Hefner was a trailblazer and trendsetter. Not only did he found the Playboy empire, but he also pioneered the pajamas as street style trend that’s become popular with stars including Rihanna, Gigi Hadid and Selena Gomez.
Hefner passed away at age 91 on Wednesday, September 27, but his style and legend live on. Scroll through to see the icon’s laid-back fashion moments throughout his epic life.
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Hugh Hefner was a trailblazer and trendsetter. Not only did he found the Playboy empire, but he also pioneered the pajamas as street style trend that’s become popular with stars including Rihanna, Gigi Hadid and Selena Gomez. Hefner passed away at age 91 on Wednesday, September 27, but his style and legend live on. Scroll through to see the icon’s laid-back fashion moments throughout his epic life. PHOTOS: 45 Sexiest Celebrities Who Have Posed In Playboy!
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He accessorized his pajamas with a pipe for his cameo on Pink Lady in March of 1980.
Credit: Ron Tom/NBC/NBCU Photo Bank via Getty
He posed with Playmates in a black and gold getup during the same Pink Lady appearance.
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For his cameo in Fresh Prince back in 1993, Hef sported green pajamas to meet Will Smith, Karyn Parsons and Alfonso Ribeiro.
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He rocked a red robe for The Hoppening to benefit AIDS Project on September 17, 1994.
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Who doesn’t want to wear their pajamas to a party? Hef chose purple silk pjs and a red robe for the APLA Party in 1996.
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The host with the most struck a pose by a giant chandelier at the Playboy Mansion on February 17, 1999.
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The Girls Next Door star was joined by two bunnies, including Holly Madison, as they filmed a commercial for the X Games on May 6, 2003.
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He posed with Kendra Wilkinson, Bridget Marquardt and Holly Madison during movie night at the Mansion on June 18, 2004.
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Hef looked comfortable and classic in a red robe, black pajamas and black slippers on November 17, 2005.
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He posed for a photo at the legendary Playboy Mansion on November 17, 2005.
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The Playboy founder rocked a red robe and silk pjs for the DVD premiere of Hot Tub Time Machine on June 26, 2010.
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He chose an all black ensemble with red lapels to host the 6th annual Kandyland event at the Playboy Mansion on June 25, 2011.
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He donned matching purple silk pajamas with his son Cooper for the Annual Midsummer Night's Dream Party on August 16, 2014.
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