I've got the Showers Pass Transit Jacket. Sizing seems to be a bit on the large size, but it is ok. I also had the earlier Burley Jacket.

Anyway, I typically just wear the jacket over Fleece. It is reasonably waterproof (good for Oregon). And, I'm fine from about 20°F up to about 40°F, and even into the moderately warm weather. Zip up the sleeves for really cold weather, otherwise they're normally open.

It can be chilly starting up, but I'm ok once I get the blood flowing. When I was in Portland, I'd start my cold mornings with a pretty gnarly hill climb that would always get me warmed up.

I also have a jacket from REI which the sleeves come off completely. I find it is a bit of a pain as they're always trying to come apart at the wrong time. But, some people like the vest option.