I rode the Oregon Randonneurs New Year's Day 200K - which was actually 206k (128 miles). It was coooooooold. 28 degrees for the 7:30am start. High of 35. I have Raynaud's Syndrome quite severely and really suffer in the cold, so apparel is absolutely critical for me. Fortunately, I know where to get some great stuff. :-)
The run down, from head to toe:
Sugoi Midzero Balaclava http://www.teamestrogen.com/prodSU_92917U.html
Louis Garneau Helmet Cover http://www.teamestrogen.com/prodLG_1083072.html
Tifosi Envy Sunglasses http://www.teamestrogen.com/prodTI_TV031.html
Craft Pro Zero Extreme Base Layer http://www.teamestrogen.com/prodCR_1900244.html
Smartwool Full Zip Wool Jersey (sold out)
Gore Bike Wear Windstopper Phantom Jacket http://www.teamestrogen.com/prodGB_JPHALO.html
Pearl Izumi Amfib Gloves http://www.teamestrogen.com/prodPI_8819.html
Icebreaker Wool Cycling Knicker (new for S'11 - not yet on market)
Pearl Izumi Amfib Tights http://www.teamestrogen.com/prodPI_4355.html
Smartwool knee high snowboarding socks (we don't sell the snowboarding socks, but they are among the thickest socks SW makes. )
Little Hotties Foot Warmers (bottom of feet) http://www.teamestrogen.com/prodIP_07005.html
Little Hotties Toe Warmers (top of feet) http://www.teamestrogen.com/prodIP_07008.html
Sidi Goretex Winter Booties http://www.teamestrogen.com/prodSD_10210.html
Pearl Izumi Shoe Covers http://www.teamestrogen.com/prodPI_9292.html
homemade bootie liners!
I run cold, so while many people would roast in what I was wearing, for me it was perfect. I'll also say that as I was set up, it was very easy for me to regulate my ventilation as I warmed up and cooled down. I zipped and unzipped the jacket and pit zips on the Gore piece as needed. The balaclava stretches really well, so when I was cold it was over my mouth, when I was warm it was under my chin.
I carried extra clothing (dry bra and base layer, which I changed at the halfway mark, so that I'd have a fresh dry layer next to my skin), extra gloves, extra beanie, more toe warmers.
Homemade bootie liners: these are made out of hot water heater aluminized bubble wrap (the stuff you wrap your hot wat heater in, to insulate it). Jeff got a wild hair and made them for me a few days ago. He says they are rated R-3. :D They certainly worked, in combination with everything else on my feet. I was out for 10 hours. The little hotties finally gave up the ghost around 8 hours, and that was when my feet started to chill. But I was so grateful for 8 hours of warmth. Usually the little hotties alone help, but aren't quite enough for me. Again, for most people, this would be way overkill, but I spend much of my day (inside and outside) struggling with the circulation in my extremities, so I'll try just about anything.

