Hefner, once called the "prophet of pop hedonism" by Time magazine, peacefully passed away at his home, Playboy Enterprises said in a statement.
Hefner was sometimes characterised as an oversexed Peter Pan as he kept a harem of young blondes that numbered as many as seven at his legendary Playboy Mansion.
Here are some images from Hefner's life:
Hefner pictured amidst a group of Bunnies, at the flagship Playboy Club, in Chicago, circa 1960. (AAP) Source: AAP
Hefner looks over proof sheets for his magazine Playboy, in Chicago, Ill., on June 20, 1961 (AAP) Source: AAP
Hefner talks about his coming late night TV show, Playboys Playmate Party in 1977 (AAP) Source: AAP
Hefner poses with "bunny-girl" hostess Bonnie J. Halpin at Hefner's nightclub in Chicago in 1961 (AAP) Source: AAP
Hefner and his girlfriend Barbara Benton, 19-year-old co-ed turned actress, surrounded by Bunny Girls in 1969 (AAP) Source: AAP
Bunny Betsy, left, feeds Hugh Hefner a piece of congratulatory cake after he was awarded the 1,716th star in the Hollywood Walk Of Fame, 1980 Source: AAP
Hefner in 1986 with a group of Playboy bunnies at the Playboy Club (AAP) Source: AAP
1982: Hefner with a Playboy Magazine and Playboy video (AAP) Source: AAP
Hugh Hefner and some of his Playmates (AAP) Source: AAP
Hefner and former Playboy Playmate of the year and US Actress Pamela Anderson (L) in 2003 during the 50th anniversary of Playboy (AAP) Source: AAP
Hefner photographed at the entrance to his movie theatre at the Playboy Mansion in the Holmby Hills area of Los Angeles Friday, April 7, 2006 (AAP) Source: AAP
Hefner at his 80th birthday in 2006 (AAP) Source: AAP
Halloween party In this photo released by Playboy, from left, Kendra Wilkinson, Bridget Marquardt, Hefner, and Holly Madison in 2007 (AAP) Source: AAP
Bill Cosby, perennial host of the Playboy Jazz Festival, right, and Playboy impresario Hugh Hefner greet each other in 2008 (AAP) Source: AAP
Hefner at his home (aka Playboy Mansion) in Beverly Hills, Calif. on Sunday, Oct. 13, 2011 (AAP) Source: AAP
Kendra Wilkinson, Hugh Hefner, Holly Madison and Bridget Marquardt, from left, pose poolside at Hefner's Beverly Hills, Calif, estate (AAP) Source: AAP
Crystal Harris (left), Hugh Hefner and Cooper Hefner (right) during Playboy's 2013 Playmate Of The Year luncheon at The Playboy Mansion (AAP) Source: AAP
