Did you start cycling in the '70s bike boom?
My wife drove by my club ride one day and laughed at one of our friends who was riding with us in jeans, flannel shirt and his heavy duty Timberland boat shoes with Vibram soles. He wears cycling shorts sometimes but when he rides to work he wears street clothes like we all did in the '70s. And no matter what he wears, he rides like an animal.
I suppose you could call it that. I never thought of myself as being a "child of the bike boom". But, Dad started doing a pretty wicked bike commute in the mid 70's, and I would have just started riding in the mid 70's, but was already cranking out at least a few miles in the late 70's.
Perhaps it was a different era back then. Mom sewed together a pair of bike shorts for my brother to race in, but most of our riding was in ordinary clothes. I don't think I got the racing shorts.
Anyway, I doubt that I'm your riding buddy, but he sounds like great fun