It is true that everyone reacts differently to the cold. For me, 30-40 degrees is cold, not cool. I'm still trying to figure out how to dress right for temps in the high 40s/low 50s. I tend to have problems with my feet being cold.
I have a friend who's a total polar bear. He rarely will say that it's too cold to ride. He's also a big fan of wool. One thing he recommended to me recently was that I should get a wool cap. I just bought the Ibex Coppi cap, which is so cozy I think I just might sleep in it this winter. It fits well under my helmet. http://www.teamestrogen.com/prodIB_852.html
For jerseys, he recommends Wabi Woolens. They're a bit pricey for me.
Last winter several friends recommended that I get booties. I bought a pair (on sale) in the spring. I haven't worn them yet, but I think this Wednesday I will be trying them out on my post-work ride.
Last weekend I did a ride in the rain. Temps were in the 60s but knowing how cold my feet get, I decided to try putting Saran wrap around the front of my feet inside my shoes, and then put toe covers on the outside. This worked well to keep my feet warm and dry. (It was light rain; I imagine my feet would have been wet if we'd had a real downpour.)
I have a small handlebar bag that I use to store extra layers if I'm not wearing them.
Also, I created a file in Notepad on my pc where I takes notes on cool weather rides, including the date, time of day, weather conditions, what I wore, whether I was comfortable. This helps me make decisions on what to wear in various conditions, which makes it more likely that I will be able to convince myself that I can be comfortable even if it's cold outside.
- Gray 2010 carbon WSD road bike, Rivet Independence saddle
- Red hardtail 26" aluminum mountain bike, Bontrager Evoke WSD saddle
- Royal blue 2018 aluminum gravel bike, Rivet Pearl saddle
Gone but not forgotten:
- Silver 2003 aluminum road bike
- Two awesome worn out Juliana saddles