What works for me down into the 20'sF.:

Head (any mixture of these):
Wool skullcap
Wool balaklava
Wool cycling cap
Helmet (great wind blocker for me).
Sunglasses by day.
WalMart display clear plastic glasses at night.

Upper body:
Wool baselayer shirts.
J&G breatheable rain jacket (acts good as windshell so wind wont cut thru wool 
layers) It is very vented. Not perfect but works for me on long rides. Without 
it I can see redness on trunk where wind penetrated the wool. So the jacket has 
been great for me.

Hands:
Any gloves that work. Doesn't have to be cycling specific. But rubber on 
fingers helps grip brake levers.

Legs:
Wool baselayers.
Rivendell MUSA long pants.

Feet:
Leather Nike sneakers on flat pedals.
Wool socks.
I don't need two layers of socks until I get doen into the 20'sF.

Caveat:
After 30 miles in the cold my thighs and knees sometimes complain.
But sub-20 mile commutes and other riding I'm fine with any combo of layers 
with the above.
For distance riding I'd definitely use wool tights with Boure tights over top. 
Better for keeping legs warm so far on longer rides.

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