ok, my advice would be to look online. i live in australia, but i love love love looking at the winter fashion (not required here!!) on revolveclothing.com. you can get some really good ideas about different styles, how colours work etc and then modify it to suit your style and purpose.

i am not sure if there are sites like that for an older demographic, but try googling things like "winter fashion look book" and you should get a few websites coming up.

i am a wimp even in an australian winter (it was 20 degrees celcius today - too cold for my bones LOL). i am heading to japan over xmas (will be snowing there) and i am having panic attacks at the thought.