The thing that's funny about modern equipment is how many people yearn for "vintage" equipment. While I have nostalgia for old stuff and own some of it, I wouldn't trade any of my current 'kit' for vintage bikes and gear. I still have the second bike I raced (in restored condition), a wool Renault jersey of Greg Lemond vintage that is still quite serviceable, the last leather hairnet that I wore in races, and a NOS pair of Addidas lace-up, leather shoes with adjustable, screw-in cleats. Guess I'm ready for the next Eroica California if the 14-18 straight block on the bike is sufficient.
When I started racing, I could barely afford to buy shorts. My mother is an expert seamstress and she copied my store-bought shorts and used chamois that I bought at the local automotive parts store to pad the shorts. She also repaired my purchased short with the same "automotive" chamois. Sometimes I would apply Vaseline to soften the chamois after washing but generally I just softened them through riding.
Side story: A forum member once tried the same brand and model of modern TT saddle that I use. He said it felt like a knife up his a$$ and that I must have an iron a$$. Maybe.
Skiing was actually my first favorite sport through my dad's love of skiing. Like Racer Ex, I had leather boots with bear trap bindings on wood skis. Graduated to cable bindings before switching to step-in, release bindings and fiberglass skis. Tried to be a ski racer for a number of years but trying to bend 200 cm skis through slalom gates when you're 5' 7" and 120 lbs (or less) was kind of a losing game. I was better pedaling a bicycle uphill at that time.
Maybe I'd be a better Masters ski racer than a Masters bicycle racer now.