It truly takes BIG talent to pull off a look so simple. The reason being is that some people just try way too hard to be stylish and casual that it ends up being... on my 'FASH, CRASH AND BURN' posts.
Check out Detroit native rapper BIG SEAN who pulls off a simple look such as a white tee, dark denim jeans, simple sneakers, and a "man bag" to style. Keep in mind fellas, there is NOTHING WRONG WITH A MAN BAG... it just depends on whether it looks more like a lady's purse is when it's a problem.
This rapper also sports his simple jewelry (chain), YSL pocket tee with a red handkerchief in the pocket, TI$A sneakers ($125) and an MCM duffle bag.
It just don't take much to look good. If it's hard for you, you should study this...