Lifestyle Style Hugh Hefner's Most Iconic Robe-Wearing Moments Hugh will be remembered for creating the incomparable Playboy magazine, hosting his legendary Playboy mansion soirées and of course, for his fondness of wearing smoking jackets wherever he went By Colleen Kratofil Colleen Kratofil Colleen Kratofil is a former style editor at PEOPLE. She left PEOPLE in 2022. People Editorial Guidelines Published on September 28, 2017 12:25PM EDT Close 01 of 12 STYLE SETTER Long before daytime pajamas became the trend du jour, Hugh had made it his signature look for decades. The business mogul was so devoted to his comfy-dressing ways that you can find him just about anywhere, at just about anytime, wearing his silk threads. 02 of 12 MOVIE NIGHT Hugh was known for hosting movie nights in the mansion, at which his uniform was a comfy pair of black silk PJs. 03 of 12 SITTING BY THE POOL Jeff Robbins/AP/REX/Shutterstock Hugh traded silk for terrycloth when pool-side. 04 of 12 SHOWING OFF HIS WORK When you have a hugely successful publishing empire, you can wear whatever you want to show off the finished product. 05 of 12 GETTING GROOVY Hugh knew a pajama party was always a good idea. 06 of 12 TV CAMEOS Yes, that's Hugh with Will, Hilary and Carlton doing a cameo on The Fresh Prince of Bel-Air wearing … what else? His quintessential pajama set with robe. 07 of 12 AT A CASINO So these slot machines are technically inside his mansion, but he still made a case for gambling in your PJs. 08 of 12 IN A BOXING MATCH James Caan may have thrown a good shot, but Hugh dressed the part for a boxing match and that makes him a winner with us. 09 of 12 ON THE RED CARPET His secret to making pajamas look chic for a big event was matching his jacket lapels and cuffs to the carpet. Genius. 10 of 12 HALLOWEEN Broadimage/REX/Shutterstock While Playmates celebrated Halloween in barely-there outfits, Hugh opted for his robe. 11 of 12 HALLOWEEN TAKE 2 … and sometimes threw in a hat for some pizzazz. 12 of 12 HALLOWEEN TAKE 3 Charley Gallay/Getty And finally convinced Playmates that his comfy-over-sexy mentality was clearly the way to go.