Last year, my first in Portland, I bought a very uncool North Face jacket. I was determined to bike everywhere and needed something practical, sporty and, most importantly, rain proof.
I felt like crap every time I put it on.
This year I was determined to find something a little bit more fashionable. My first find: this great Spiewak jacket at Local 35. Love that it's fitted. Love that it has a tiny gray herringbone print. Love the buttoned pockets.
Spiewak, $140 at Local 35

My second find is a more suited to strolling than cycling. Still, this Trovata wax-coated trench repels rain and looks very sharp. Get it at Parallel Boutique.
navy_trench.jpgTrovata, $374 at Parallel Boutique

Lastly, Lizard Lounge has three different jackets from Scapegoat. They're as technical as my horrible North Face jacket, but in a slim silhouette that's lot closer to cool. These jackets are on the warm side, worth it if you're going to be biking all winter and still want to keep a measure of style.
Scapegoat, from a selection at Lizard Lounge