last year I rode consistently thru the summer, fall, winter & spring & wound up using some stuff I had kicking around the house but also bought some new stuff. I'm a fan of cycling specific stuff but sometimes I can make do w running stuff or other outdoor stuff. cpl things/combos I wound up using more than once were a standard pullover hoodie. a zip-up would be more useful, but flipping the hood up & down was surprisingly helpful. when it got really cold, this North Face fleece jacket (w/pit-zips) & Novara cycling wind break w sleeves zipped off