Notable partners: Mila Kunis, Demi Moore

The interesting thing about Ashton Kutcher is that it actually seems like he tries to improve his style. He reinvents his look quite often, never really sticking to one look or trend. Theoretically, that sort of thing should work and should eventually help a person develop a distinct personal style that actually works, but not so for the actor. In the past, such experiments just resulted in bizarre garments like camo kilts, suspenders, pedophile-like mustaches, really deep V-necks, and wide-brimmed hats.