"There is, in American culture, a premium place on being 'nice.' Although this can make life easier in many ways, it is simply hell for developing style. Style requires a 'like it or lump it' attitude towards one's public. Your public includes husbands, wives, girlfriends, boyfriends, mothers, children, workmates, classmates, and the people who pass you on the street. You do not exist to win their approval. Does this mean we think you should wear a cocktail dress and saddle shoes to work because that's what you love? Well let us invoke the Blackstone Ratio: 'Better that ten guilty persons escape than that one innocent suffers.' In other words, if adjusting to and discovering your personal style results in a few funny outfits, so be it. What is important is that a space is created for a person to embrace who she truly is. Even if, and it pains us to write this, it includes saddle shoes."
From Tim Gunn: A Guide to Quality, Taste, & Style