Well, inland in northern CA and Oregon can be both colder in winter and warmer in summer - even not very far inland. So when you are deciding what places you like, be sure to check out temperatures online for specific areas.
On gloves, drugstores start to stock gloves by the cash registers as winter comes along - I had a few of those types of pairs, cheap, warm knit gloves. You can also get lined leather gloves at some expense. Not knowing really what you'd be doing, going up to nearby mountains? it seems to me the ordinary gloves would be fine - you can always buy a better pair when there, or if and when you move. Sorry, you'll have to look on amazon yourself...
(I'm not clear where you are going to vacation.. Portland?) In my old area, folks are pretty casually dressed most of the time. Parkas, various jackets, jeans, work boots, sneakers - though sometimes other types of shoes/clothes. I think of Portland and Seattle (which I've been to for only a few weeks) as somewhat similar. We'll see what other posters have to say.