I can understand why television shows like What Not To Wear exist. Because how do you figure out how you ought to dress yourself if you don't already know?
Maybe fashion-sense in humans is like birdsong for birds: there's a temporal window during which you're able to acquire it (high school? college?), otherwise you're sunk. Or is it another of these abilities you have to be born to? (And, to pick up the previous post, is there a vampire out there whose talent is super fashionableness?)
I found a helpful site telling me how to dress if I am small (I am), and where to shop. It was only later I discovered that the site was written mainly with female-to-male transsexuals in mind.
I'm not transsexual, but I feel just as out-of-the-loop when it comes to male fashion. Thank you, Hudson's FTM Resource Guide!