Nostalgia: When one pant leg rolled up was cool - The Standard

This fad originated from American bike messengers who rolled up to avoid their pants from

You rolled up your pant leg without fully knowing it's meaning, admit it. : r/90s

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Rolling up one pant leg like LL Cool J. : r/nostalgia

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One pant leg up trend (and bonus oversized jersey) : r/90s

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I'm sure there was a reason why the first person to roll up a pant leg, 90's Streetwear Fashion