You are all awesome and this is such great info -- thank you! I'm trying to minimize cost where I can (although I just dropped a silly amount of money on locking bicycle bolts, fenders, etc.) and went to GoodWill yesterday to look for some athletic wear. I found a few running shirts, as well as some Nike running shorts with built in spandex-ish liner that I'll probably try out this weekend on a test ride. There is no chamois in them, but I think it will give a good idea as to if I need one or not.

For rain and cold, I also own a windbreaker and some long-sleeve thermal shirts that should do it I think.

As it's still pretty cold in Seattle (mid 30s to low 50s) shorts alone probably wont cut it entirely... I think jeans would be too uncomfortable. Any ideas here? Dedicated tights and/or some kind of stretchy pants?