: Where does the fear of wearing boots come from? Rewind back to school days. Turning an old pair of bluejeans into cutoffs for the summer and being shouted at by Mom, "You're not leaving the house like that, young man." Borrowing a friend's Levi jacket and Dad says "Take that off this instant, you are not a juvenile delinquent, now go put on some proper clothes." Snow-boots were OK if there was snow, workboots were only to be worn for working, and so on; constantly being pestered by Mom and Dad about anything outside the norm. So you learn to keep the fun things like motorcycle jackets and boots hidden away, and not to wear them in public anywhere someone might report back to your parents about what you're wearing. That's why I was afraid to wear boots or leather or a Levi jacket until after high school.
I remember my high school days, in the '50s, when the "uniform" for the really cool guys was the black leather biker jacket, very tight 501s and engineers boots. My mom and dad were working class, and not at all concerned with middle class values. (whatever they were) What I chose to wear had only to be clean, in good repair and cover me decently.