I remember growing up with no winter hats, or elderly bobble winter hats that I wouldn't be caught dead in at school, a thin autumn jacket that I wore all winter, and yep, pastic bags in my shoes or folded newspaper to add to the soles. And I remember going to one skiing class and being so cold I could hardly move. My parents weren't really stingy or poor, just clueless about how to dress well in winter to actually do something outside, not just survive moving from door to door, and they were very big on non-consumerism, jumble sales and recycling everything. Which is fine when you're an adult and can make your own decisions about what you want to wear, a little harder for a 14 yr old in the 80's.
My son has the most functional winter clothing I can lay my hands on. And nothing expensive or high-fashion, but clothes that no-one will ever point out don't fit in.
Pardon the hijack, this sort of hit a nerve
Winter riding is much less about badassery and much more about bundle-uppery. - malkin
1995 Kona Cinder Cone commuterFrankenbike/Selle Italia SLR Lady Gel Flow
2008 white Nakamura Summit Custom mtb/Terry Falcon X
2000 Schwinn Fastback Comp road bike/Specialized Jett