I really don't think it's a question of In or Out. Fashion is not the same as Your Style. If it works on you, do it.
I recently bought a couple of dresses that are so short you normally think they are for twentysomethings, not a 57 yo man. But I get told over and over "You totally have the legs for it. Go for it. Just don't drop anything that you have to bend over to pick up. You don't want to show off your underwear, too." LOL. And they do look cute on me.