Yes, that is what I am suggesting, plus a hat. Just – as others have said – find a synthetic T-shirt instead of a cotton one. It doesn’t have to be a fancy technical fabric; an old nylon running shirt is fine. Maybe a short sleeve one in the summer, a long sleeve in the winter. You are right about the bottoms issue. I’ve seen very few people bother with waterproof pants (probably because of expense, bulk, or heat), but you will get soaked from the waist down in really wet weather. Instead of getting waterproof pants, however, it may be more practical to get some nylon pants (track suit bottoms are fine) that will dry out quickly, and then pack some polyester long johns or old tights/leggings (again, synthetic fabrics only) in a ziplock to change into whenever you get to shelter. Then let the nylon pants try out. More generally, I don’t find an insulating layer on the legs necessary during physical activity. Plus it can be hard to take on and off, and it is important to keep regulating your layers so that you don’t sweat too much. The chill from your sweat is what can really make you cold later. (That’s also why I like having a hat – it’s easy to take on and off and can change your temperature a lot.) Having an insulating layer can be good for sleeping or around camp, but your the long johns / tights can serve that purpose: you can wear them to sleep or double them up with your windpants for around camp in severe cold.