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I do this when hiking something..
Or in the morning when im constantly adjusting my boots...
It's not a big deal
and im pretty sure anyone who rolls like this doesn't care if you dig it or not.
I don't really care how other people dress, to each his own, but this seems like a bad idea as far as function goes. I know that if i rolled my pants up while i was skiing (different for walking around if you don't want to rip up your pants) then i would get a ton of snow in my boots which would make me cold, uncomfortable, and ultimately a worse skiier because of these things, so i don't get it