I think you can get away with not too many clothes for the winter:

60F and up - bib short, short sleeve jersey, open finger gloves, skullcap, socks, shoes, helmet
50 - 59F - bib short, knee warners, long sleeve baselayer, short sleeve jersey, open finger gloves, skullcap, socks, shoes, helmet
40 - 49F - bib short, bib tight, long sleeve baselayer, long sleeve jersey, full finger gloves, winter cap, socks, shoes, shoe covers, helmet
30 - 39F - bib short, bib tight, long sleeve baselayer, long sleeve jersey, 2nd long sleeve jersey, winter gloves, winter cap, socks, shoes, shoe covers, helmet
20 - 29F - bib tight, thermal bib tight w/chamois, long sleeve baselayer, short sleeve jersey, long sleeve jersey, 2nd long sleeve jersey, winter gloves, winter cap, socks, 2nd pair socks, shoes, shoe covers, helmet
19F or lower - ride indoors (trainer or rollers)

Also have a rain jacket for rainy days that counts as two layers. The long sleeve baselayer is a compression shirt. Socks are usually marino wool.