What I do is choose someone with a similar body type to mine, who I think dresses well. Clean, respectable, but not in your face, y'know? And I try to buy similar things. This is something I think would work for anyone.
If your choice makes you look out of step with the times, well, that can even work to your advantage. Older clothes tend to be more flattering, if they fit properly of course. With confidence and a sense of humor you can carry off almost any style. People may even think of you as stylish if you can do it without acting awkward. (Shoot, if you're looking to impress people a generation older than you, this can seriously open doors.)