You’re talking about an urban fad (and a pretty long-standing one, too) established by the rapper/actor L.L Cool J. There is no ‘why’ behind it, I don’t think, even though it is usually the right pants leg that is rolled up, and all bike riders know that this is leg that h often gets caught up in the gears.
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Name : T.R., Gender : F, Race : Black/African American, City : Newark, State : NJ, Country : United States, Education level : Over 4 Years of College, Social class : Middle class,