So the weather is on a cooling trend. It was 27 degrees when I left home this morning at 6:45 headed downtown for coffee and a bagel. That’s not even close to too cold to ride a bicycle. I’m not sure I’ve ever experienced too cold in Springfield (seeing as how it’s a matter of dealing with the cold rather than worrying about it). I think 16 degrees is the coldest I’ve dealt with here (reminder: I don’t ride in ice or snow because I’m too lazy to buy or make studded snow tires — so I walk instead).
The keys to staying warm for me are my head and hands. I wear a fleece ear-cover thingy under my helmet (which I wear most of the time in the fall and winter because one of my risk criteria — darkness — is nearly always in play as is criteria #4). I also have a fleece skull cap when it gets into the teens. Both are adequate for the short distances I ride (usually no more than 20 minutes to most destinations in the urban core).
I prefer leather gloves with Thinsulate. You can buy these at most hardware stores.
And nothing beats leather, IMO, as a wind-breaker. My leather jacket also has Thinsulte, so, yeah, I stay nice and toasty. I generally use a scarf, too, in the early part of the winter before I become more acclimated to the cold. By February, a 27-degree morning will hardly be worth a moment’s notice