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.
Hugh was known for hosting movie nights in the mansion, at which his uniform was a comfy pair of black silk PJs.
SITTING BY THE POOL
Hugh traded silk for terrycloth when pool-side.
SHOWING OFF HIS WORK
When you have a hugely successful publishing empire, you can wear whatever you want to show off the finished product.
Hugh knew a pajama party was always a good idea.
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.
AT A CASINO
So these slot machines are technically inside his mansion, but he still made a case for gambling in your PJs.
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.
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.
While Playmates celebrated Halloween in barely-there outfits, Hugh opted for his robe.
HALLOWEEN TAKE 2
… and sometimes threw in a hat for some pizzazz.
HALLOWEEN TAKE 3
And finally convinced Playmates that his comfy-over-sexy mentality was clearly the way to go.