Warm weather (this is 5 to -8 usually)
Polypro underwear
Fleece Pants
Wool Sweater (maybe a fleece if it's a windy -10)
Light wool work socks
Leather work boots if there's no snow, cheap rubber Kamik's from Canadian Tire if there is
Colder Weather (-9 to -20)
Polypro underwear
Thick red/black plaid Mackinaw Pants (may throw a pair of fleece pants under if I plan on sitting when its that cold)
Heavy jacket to match the pants [8D]
Heavy wool sweater
Two pairs of thick Remington socks (advertising got me good
)
Same cheap rubber Kamiks
EDIT: Temperature's in celcius