I wear the same shoes year round. I wear the same Merino(70%) wool socks year round. I just add neoprene booties below freezing. Above freezing I use neoprene toe warmers. Yes the booties are a bit of a pain to deal with but not as big of a pain as the pain in the foot from cool feet. I have ridden plenty of 100 mile days during the cold winter months up here in New Hampshire and I rarely take a day off the bike. Get use to dealing with the booties, neoprene booties, not these junk nylon booties, or whatever those paper thin booties are made of, that some companies make. You want neo booties. I would go for the wool socks as well.