The only reason why I started cuffing some my jean(s) is it looked more proper. It gave a smoother silhouette. I also noticed that usually the older generation always have pants that don't stack so aggressively to that of the younger generation.
Really depends on the shoe...alotta times with hi tops I will do a small cuff. Not really a big fan of the old school double/triple farmboy cuffs...IMO if you have enough length to cuff them that much they are too damn long!
