The older military surplus is useless. I've been in the Army for almost 14 years, and the quality of the older cold weather gear was atrocious compared to what we use now. I just wouldn't waste your time, not to mention, with the faux love affair joe public has with the military these days, you won't get a good deal on crappy gear.

Check Nashbar, Sierra Trading Post, Backcountry , etc. You'll do much better that way. Invest a little coin now for long term comfort in the long run. For example, I just bought a new winter jacket from Sierra Trading Post that was originally $300, after their discount and an online coupon for another 30% off, I spent less than $140 for it. I am confident it will outperform any of the gear I have in the closet from my various travels.

I'll second the previous poster on the bit for base layers. Don't worry about cycling specific stuff. Base layers are base layers, just make sure they wick.