Don't spend money twice Yes, bicycle specific clothing can be expensive but it lasts forever. I have equipment that is going on 15 seasons and is still going strong. The stuff you buy at HellMart isn't going to last that long. Buy a few articles of bicycle specific clothing at a time...jackets and tights are the best places to start...and you'll have a hell of a wardrobe in no time. Buy on sale when you can Performance house brand stuff is a very good value and lasts just as well as the much more expensive stuff.

In terms of use, think of clothing as solving several specific problems that may be at cross purposes. You want clothing that is warm when you start but not too warm when you've been riding for a while. You want clothing that moves moisture but you don't want the wind evaportating it too quickly. You want clothing that can be adjusted to dump heat but keep heat in when you need it.

For starting your ride, you want to a little cold for the first few minutes. Start too warm and you'll be sweating in no time. For the most part this means avoid thick fleece jackets. They provide way too much insulation. Two lighter (noncotton) layers will do the same job and allow you to remove one if you need. Try to find shirts with zippers at the neck so that you can vent them (that's why bicycle specific clothing works well).

Wind is probably your biggest foe. It evaporates moisture which takes heat with it. Often I find that a wind blocking layer, does as much as an insulating layer.

Most of this applies to the chest. I find that I need little in the way of covering on my legs since they are generating lots of heat.