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.