For bottoms, I try and stay away from anything cotton that will soak up a bunch of water. I have a few pairs of REI pants that are 100% synthetic and super roomy. Personally, I can't stand playing in shorts (even in summer). I hate ticks, and am painfully allergic to poison ivy, oak, etc. I never got hot once this summer, or at least no hotter than if I were wearing shorts, even when it got up to 100. I do the same with my top layer: some kind of moisture wicking synthetic material. It's all about moisture and temperature regulation. In the summer, they keep you cool and dry and in the winter they keep you warm and dry. I can't stress how important it is to keep from sweating heavily while out in the cold. When your warm and moving you're fine, but once you slow down you get very cold, very fast. Hypothermia isn't a big risk when your going back to your car, but it also sucks to be cold and clammy on the course.
I like to layer as it gets colder. I'll add long, but very lightweight thermal underwear underneath my pants and wear long sleeved thermal underwear under whatever shell I've got on. I'll use a rain shell if it's going to be soggy, and also rock the knee-high gators. Other than that, it's fleece all the way. It breathes great and will insulate when wet (to an extent). The downside is that most fleece sucks in the wind. Thinsulate Windpro is my personal favorite. I've hung my arm out the window at 45 mph and even though my hand turned into an icicle, my arm felt warm and toasty.
Finally, merino wool socks! Merino wool is a superb insulator when wet, it moisture wicks, and it breathes very well. Smartwool socks are the best brand, but at $12-$18 per pair, they're a little out of my price range. Costco and Cabellas both carry generic brands that are more like $5-$7 per pair.
PS- Costco sells jumbo packs of hand warmers for a price that will make you hate the gas station punks that are charging you two bucks a pack.
