I should invest in some thermal underwear someday. I've never needed it. Had some when I was a kid, but it just made me too hot. One pair of wool socks, one pair of fruit of the looms(boxers or briefs, your choice), one lose sweatshirt, one pair of jeans. Maybe a pair of sweatpants if it is under 15. One good pair of coveralls(like carharts). A good pair of waterproof boots with felt liners(lose fitting). And one very old, raggedy parka with a snorkel hood from Sears that I've had since the '70's. A pair of mittens if the wind picks up. A lose hat with face mask if it gets to 0. Maybe a secone hat if it gets to -5 or -10.
I think the parka is the key. It is windproof and covers from my mid thigh all the way up over my head. The snorkel hood makes a tunnel to warm the air before I breath it, but tends to fog the glasses. I can sit with my back to the wind for a few hours before I have to start sipping on the hot tea or cider(just switched from cold pop to hot drinks last year).
I really enjoy the cold. Once you feel the hair in your nose start to freeze, it is usually a little below zero. That's the time I like best. /forums/images/graemlins/wink.gif