2. Oscar Wilde
Dublin, County Dublin
To his contemporaries, Oscar Wilde's flagrant manner of dress was as well-known as his plays, novels, and poetry. His conversational wit was supposedly as sharp as his opulent Victorian dress, and the native Dubliner flitted through London's highest social circled decked out in the illest garb of the day. If you're ever doubting the notion of trying something flamboyant or outrageous, just look at what Wilde rocked on the daily for a moment of inspiration.