No disrespect intended, but I have lived without a car for over four years and crossed the country (walking through mountains while it was snowing) earlier this year in winter in sandals. My experience: Being healthy enough means you tolerate a wider range of temps and climatic conditions without changing clothes. My sons essentially live in t-shirts, shorts and sandals year round. My oldest has walked to the store in the snow in a t-shirt, shorts and galloshes.
I feel like I understand how those eastern monks walk around in saffron robes in winter in the mountains.
It's easy to do in San Francisco where it never gets really hot or cold and the only precipitation is a mild drizzle.
If you're in upstate NY, however, you need to design a system that adapts to climate conditions from -15 to 110F.