Portland's Pearl District is the swank-yet-hip warehouses-to-loft-condo district. Plenty of folks on bicycles, real and faux hipsters in abudance and at the same time, women dressed to the nines in Audi A3s.
The standard uniform for the average "man in the coffeeshop window" is a dark gray mock turtleneck and funky reading glasses, with a North Face or Patagonia soft shell over the back of the barstool, usually hunched over a Powerbook. I hate to make stereotypes, but it's true. If I get the guts I'll document it, but I still have a problem sticking cameras in people's faces.