Sources suggest that Hugh Hefner's iconic smoking jacket look started in the late 1960s. At that point, Playboy was a roaring success and Hefner moved his office into his bedroom to make things easier. Then he realized he could wear them all day.
"I started wearing them all the time because I was working at night, and then I started wearing them when I entertained," Hefner wrote in The Daily Mail. "I realized I could get away with it. Then, of course, people were disappointed if they didn't find me in pajamas."
He reportedly owned more than 200 custom-made smoking jackets and pajamas. He did not wear underwear underneath, according to the New York Times.
Learn more about Hugh Hefner by checking these fast facts shared by Heavy.com.