Have to call out the 1960s SX200 Lambretta posted by @damon.
In high school we all wanted to be mods. Some more than others (I had mixed feelings) but I owned (briefly) a 1970's Vespa in bright yellow, with extra mirrors and chrome. Ended up laying it down and realized it would be safer to go back to my Peugeot 50cc 2-stroke cafe racer, which was to me cooler in a dorky kind of way.
Being a mod in Berkeley, California meant wearing British bullseyes on the back of your Swedish army parka and jeans pegged with safety pins. And listening to a lot of the new ska that was coming out of the UK — and The Uptones, a local ska band a bunch of my friends formed.
It seems like a giant disconnect in retrospect, but at the time it didn't seem so. It was as natural as anything.