I truly believe fit is the most important factor . As long as what you have on is clean, the fit will make you look good. Of course quality and style will add enormously, but most important is the fit. And although I say, stretch your limits, break from your comfort zone, it doesn’t always work. Not all styles will “fit” everyone.
What works for one guy may not work for you. That doesn’t mean you can’t dress like that but you must be realistic. Which is why i say you move gradually as you experiment with looks. Instead of buying a couple of Suits like George Clooney wears, start with a blazer. If you feel good, then pursue that image. But as you continue to experiment and spread your wings, trust yourself. The fit is not just external. The “feel” is just as important. If you are not comfortable, it will extremely difficult to be confident. You don’t want your new image to be a costume, but a reflection. If The clothes are just on you, and not an expression it convinces no one, least of all yourself. You become Patroclus, the soldier who wore Achilles armor to battle.
The goal is to create, not copy.
Be The Man 