Ben Stiller

"You can trouble me for a warm glass of shut-the-hell-up! Now, you will go to sleep or I will put you to sleep. You're in my world now, Grandma.”
Happy Gilmore, 1996

Aside from his feature-length jab at the fashion industry in Zoolander, Ben Stiller has always had fun with his clothes while looking good in them. Remember his dressed to the nines Na’vi outfit at the Oscars?