I'm also from Cleveland. Today I wore a Lands End soft shell jacket over a Coolmax long sleeve T, Performance Triflex tights, a wool cap, water proof socks (for wind protection) over wool socks and MTB shoes and WindPro gloves. My feet were a little cold for the commute but otherwise comfy. I probably should wear my booties for more foot warmth.
I tend to be warmer than most and I ride pretty hard so you may want an extra layer.
The jacket I used is available from Lands End Overstocks for $15 which is a great deal. Its not as breathable as some of the better jackets but at 1/10 the price it well worth it.
http://landsend.com/cd/ov/prod/0,,2_...&CM_MERCH=SRCH
Craig