Jon Hamm
Don Draper, played by Jon Hamm on Mad Men, is a well-known character, but here we see a more down-to-earth aspect of the actor. We’ll ignore Jon’s unkempt hair for his bashful smile and the fact that he’s dressed in a tux.

His companion sported a black scoop-neck dress with a white necklace that had a hint of red carpet appeal to it. In addition to looking like they were straight out of “Mad Men,” both he and his date appeared to be dressed to the nines as well.