When I was a kid I remember being mortified by unfashionable winter clothing like hats, mittens and snow pants. For some reason it was much cooler to freeze your ass off (punny, I know).
It is still unusually cold around here, and today in Vancouver I noticed several adults wearing snow pants. My 12-year-old self was mortified for them, but my 32-year-old self thought it was a damned fine idea. I pulled a pair of David's ski pants out when I got home, and they made the evening chores much more comfortable. I didn't even need my bomber hat.