24. Hugh Hefner

Vintage 1950's Mens Robe, $40
Nike Black Sweatpants, $75
Viagra Candy, $7
Del Toro Velvet Slipper, $270

His balls are probably more wrinkled than an elephant's toe knuckle, but the blonde bomshells at the Playboy mansion seem to love him anyway. It could be his money, it could be his ability to put their naked asses on the cover, but just throw on a silky bathrobe and you'll have bunnies hopping on your dick faster than you can say "trick or treat."

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