Prbbly the biggest cuffs, but the most cuffed pants would prbbly be dylan, or john shanahan when he rolls his trousers up to his shins
Please refer to Dill, AVE and The Almighty Fred Gall n Photosynthesis...Cuffed their baggy, Diesel jeans to the point of wearing "clamdiggers". Shoelace belts got super popular after that Audio/Visual Masterpiece as well. Dylan upped the cuffed game in 2010, for sure. But Ed Templeton and Visual Sound era Stereo Sounds and Salman Agah are fully responsible for introducing the slim fit, straight legged, flooded pants style to skateboarding in the early/mid-90's. Before that, Gonz and Jason Lee ran some sharp kits in The Blind Video. Julien Stranger, his OG Antihero gang, and the Real team during Non-Fiction rocked the timeless, "vulc soles with Dickies" SF regalia. Utilitarian function meets fashion. City Lights, Baby!...The Beat Generation started it all in SF.