Lucky for me, Portland has no shortage of talented photogs willing to spare an hour of their day in the quest for style spotting. I met up with Bryan Bruchman, the guy behind HillyTown. You probably know him, since most people we photographed did. Apparently, he’s pretty popular in these parts.

We found Timmy, who works at Rogues Gallery, in front of Longfellow Books. I loved his Buddy Holly-esque specs - very retro, very geek chic. Sporting a pair of new leather Signature boots and an L.L.Bean hunting jacket, the canteen around his neck was decidedly not new. He bragged that he’s had it for over seven years and later that day, oh the irony, he lost it. But not to worry, sources tell us his beloved canteen was found again. We’ll dedicate this post in memoriam…just in case. 

Photos: Bryan Bruchman