I just went out for 10 minutes. Night @ 20 degrees wearing what my planned gear has evolved to.

Head and Face: Thin beanie cap, nose down balaclava, ski goggles, helmet.

Up Top: Long-sleeved polo work shirt, Patagonia r1, SportHill 3SP breathable running jacket with pit zips similar to THIS.

Hands: Loose, mid-weight fleece gloves with wind-block over mitts.

Bottom: Lycra biking shorts, SportHill 3SP pants like THIS.

Feet: Mid-weight hiking socks, Seal Skin water proof socks and SPD cycling sandals.

All of this gear is several to many years old and I'm sure has lost some off its effectiveness but I think I'll be good. I just biked up and down the 200 ft driveway over and over for about 10 minutes. I didn't hit the street because I don't have lights on the bike. My legs had a little bit of a chill but I wasn't even warmed up. I think if I add a sub-layer on the bottom, I'd be too warm but that's at 20 degrees. I should probably add my Smartwool base layer for tomorrow. It's a hard call. I'd rather be a little cold, rather than sweat. My feet were fine, we'll see what happens after an hour at 10 degrees. My face was a little warm but I'll be able to adjust this coverage tomorrow.

Down to the coffee shop at 7am for a city transit meet & greet (this is their bike to work day gig) and then off for another 50 minutes to the hospital where I work. Then a more rural route home with some real fast descents and a good bit of climbing. Same ride time but 20 degrees warmer.