Wool is your friend. A wool jersey over a wicking shirt can eliminate a couple of layers of synthetics. However, you can find merino wool sweaters at various clothing discounters(Ross, TJ Maxx, etc) for a whole lot less than a cycling specific jersey. Fleece jacket over that, or even a nice cycling jacket. Performance Bicycle's house brand of clothing is fairly affordable and of good quality.

Cycling tights are better, I think, than Under Armour. Winter tights are thicker, and there are even ones that have windproof panels on the front. I hate to say it again, but Performance(or Nashbar/Price Point) probably have something on sale that will work for you.

Even though I live in Florida, temps can get down into the teens. Wool socks , sometimes a neoprene sock over that, and my regular cycling shoes gets me through temps down to the 30s. Colder than that and I'll put on the shoe covers. Toe covers are easier to deal with here, as it's rarely as cold on the ride home, and they're less to pack.

Fotooutdoors is right. A heavy coat may be overkill. Wicking shirt, wool jersey, and windbreaker works down to freezing. A fleece jacket with the windbreaker over should be good for down to zero.

You will figure out what works for you. You may find you want to put platform pedals on and ride in Timberlands.