Why did everyone roll up the bottoms of their jeans in the 50's?

Multiple sizes for non-tailored clothing is a fairly recent development. I was talking to a purveyor of “cowboy” clothes who was telling me that in the 19th century, men’s off-the-rack coats came in two sizes: big and bigger. If you weren’t wealthy enough to hire a tailor, then you just made do with what was available, cinching belts and rolling up cuffs where necessary.