You would expect someone with the name Wilson Standish to be the governor of Plymouth Rock circa late eighteenth century, looking very noble in a waistcoat, breeches, cloak, and cravat. So it's fitting that Wilson Standish, Chicago 2010, from a lineage of "WASPs", is sporting Brooks Brothers indie style, wearing bow ties with jeans, custom made three-piece suits with '50s vintage neckwear and seersucker. It's ironic that his mom, an art dealer, who's very fashion-forward, embarrassed him as a kid. Despite the fact that he rebelled against her by going towards his grandfather's understated and classic genre, he maintained her penchant for standing alone, which today can simply mean attention to detail and taste. Wilson is serious about being singular in his wardrobe - he had his boat shoes made in Asia - the color schemes on the shoes are purposely mismatched - and he wears suits with one button open on the sleeve. "Old man style" is the new hip, in the world according to Wilson, where on his blog Boy Kings, he is making his mark in the Windy City in fashion and music.

If you like Wilson, you might also enjoy Raymond Chu, Dylan Treleven, or Michael Arenella.