dress up rugged fox

My pilgrimage to San Francisco starts in t-minus five hours and I need your help picking out something to wear to the Castro tomorrow night!  For those of you who don’t know, the Castro is pretty much the gayest place on the earth. It is the treasure that lies at the end of the rainbow and the hallowed ground that Harvey Milk once propped a soap-box on.

Anyways, my suitcase is still empty and my closet has thrown up all over my floor. I need an outfit to wear to the hottest club in town – and if that one is full, the hottest lesser-known under-rated club in the general area. I have photographed four outfits for you below to help me choose from! Please comment to let me know which one you like best and I will get a shot of the winning outfit when I am down there!

PS. I am assuming it is going to be sunny the entire time I am down there (even at night, indoors) hence the aviators.

Vintage Ralph Lauren jeans from Bungalow in Toronto's Kensington Market. White leather belt by Mexx.

Deep purple V-Neck by American Apparel. Cerulean blue jeans by Club Monaco. Headphones by Urban Ears.

Black T by American Apparel. Black leather belt by Mexx. Denim Jeans by Penguin.

Navy blue jacket with detachable grey hood by Guess.