Thought maybe I would chime in with a report of what worked for those who dont have a lot of fancy stuff.
Today the weather was high 38, this morning is was 33 (feels like 24).
Silk mid-weight long underwear top and bottom
Skintight cotton/acrylic underwear top, t-shirt on top
Hooded zip up sweatshirt
Wool skullcap over baseball hat
Jeans
Full fingered cycling gloves, with polypro liners but I didn't end up wearing them.
Wool Hiking socks
Hemp skate shoes
I don't have a real long commute though. I was going to wear my fleece balaclava but I didn't feel that cold once I was outside. My commute is only a mile or so, however, but I took a short jaunt through downtown and this setup was more than adequate.