I like the minimalist approach. I look for sales, but I do try and have the right clothing for the situation at hand.

I find arm and leg/knee warmers to be very useful since it can go from kind of cold to pretty warm here.

Shorts or bibs, rain jacket, wind jersey, and a fleece jacket get me through most really cold days, along with unpadded tights over the shorts.

Gloves are a must, as are shoes, even though I will easily wear stiff soled athletic shoes for a spin on the touring bike.

Jersey if I feel like it, wicking compression shirts are bought on the cheap.

Brain bucket is mandatory.

I need to order prescription shades.