Playboy Enterprises Inc said he passed away peacefully at home in Los Angeles, from natural causes.
Hefner’s trailblazing magazine helped make nudity more acceptable in mainstream publications, despite emerging at a time when US states could legally ban contraceptives.
It also made him a multi-millionaire, spawning a business empire that included casinos and nightclubs.
The first edition featured a set of nude photographs of Marilyn Monroe originally shot for a 1949 calendar that Hefner had bought for $200.
The silk pyjama-clad mogul became famous for his hedonism, dating and marrying Playboy models, and throwing decadent parties at the luxurious Playboy mansion in Los Angeles.
RIP to the legendary Hugh Hefner! I’m so honored to have been a part of the Playboy team! You will be greatly missed! Love you Hef! Xoxo
— Kim Kardashian West (@KimKardashian) September 28, 2017