"Urban nomad" is not a new concept, yet keeps morphing.
Given Portland's bicycle-centric core youth culture, clothing that won't catch in the chain is a must, but that may mean leg hugging stretched fiber of some variety. There's no preference for the women's bicycle with the lower bar, as the tunic or skirt doesn't care. These aren't hooped gowns we're talking about.
Much of the focus in this genre is on accessories, as the ninja nomad needs autonomy within cities. If you're attending a Food Not Bombs serving, or just wanting to not waste, then you won't need those plastic utensils or paper cups and plates people keep shoving at you, adding to the waste stream.
Your mess kit signals you're a soldier for the environment, on the side of trees and all that is green and good. In this way, the hippie earth mother tradition is continued, but in a somewhat more superhero vein. Maybe just chop sticks. My mom carries those around.
Which brings us to utility belts. These have been typically worn low on the waste, but there's much to be said for kidney high pouches, or holsters worn high.
The bicycle tools are typically under the seat (of the bicycle) but if you're paranoid or in a paranoid part of town, you need room on your person for small gadgets normally fixed to your steed.
I sometimes wear a money belt around the wrist or lower arm, Cuffka brand by Nirel.
The winterized outfit is the more challenging. The look derives from EMT work, where the crews need to stay flexible, able to operate equipment, fold and unfold gurneys and so forth. Para-medical meets para-military: the place to aim.
The goal is to remain compact, light, efficient, and semi-autonomous. You may be packing electronics. You may carry extra glasses, a brief case.
Ideally, this outfit is compatible with the workplace, perhaps a record store or hair salon, some public facing job. But that's Portland more than some workplaces, in that we're already over tattoos and nose rings. The fixed image of how the CEO has to look gave way some time ago.