If you are still on your way to finding an inner-sass, Simon Doonan will help you get there faster. Being a Creative Ambassador-At-Large of Barneys New York, he's got style (I mean, the man is wearing black pumps and burberry scarf in Stylecaster's 50 Most Stylish New Yorkers shoot, C'mon!) and exudes chicness.

I totally have his back on the topic of experimenting absolutely everything when you are in your 20s-30s. What's the point of wearing a bland white tee and jeans when you could be wearing a grungy black leather jacket full of studs and pins hanging off it or ten different kinds of floral in one outfit (not that everyone wants to do this). But the point is, fashion is not for the fearless and you can't possibly know what is good for you if you haven't tried and tested everything in the book.