This gentleman from Japan illustrates the Italian skill of Sprezzatura, the art of looking good, but not like you care about looking good. When I discussed the powers of Gianni Agnelli, it was rooted in his ability to disregard the rules of fashion and put forth his own.
That’s the key to this style thing, in that outside of clown suits, you really can do what you want. For instance, when we talk about “fit” being extremely important, that doesn’t mean that you have to wear slim-fitted everything. That might be your thing, but there are many others who wear wide pants, high-fitting trousers, or billowy shirts to great affect. The key is to know your body and your dimensions so that you can take advantage of what gifts you possess.
Have you seen Million Dollar Baby? In the movie, Morgan Freeman’s character describes the oxymoronic nature of boxing. When one is hit, the proper movement is to move into that punch so that you may defend yourself properly. It is against our human desires and instincts. The same occurs for how we dress when we might be a bit heavier, for instance.
Instead of wearing more fabric, less fabric, fitting closer to the body (not tight) will actually make you look better. It sounds counter intuitive, but that is the best method. If you have an athletic shape, you should actually be wearing pants that come in more at your ankle, to counteract the V-shape of your torso.
It isn’t difficult once you just stop for a second and look at what some other people are doing. Not to copy them, but look at someone with similar dimensions to yourself. Ask, “What are they wearing and how does that makes their look work?” Once you get what looks right, you’ll find shopping for yourself, whatever your body type, much easier. Critically, know what size you are (and I’m not talking Large, Medium here); find out what your neck size is, your arm length, waist, inseam, all that stuff. You’ll appreciate it later, I promise you.