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I always roll but vary the amount of roll. One turn up is my fav at the moment as we are in summer. I pair that look with my saltwater sandals. In winter two rolls and booties.
I decided to retire my boyfriend jeans after Shoptoberfest (Those pictures ...agh...) but I only wear them rolled. The unrolled look would be extremely unflattering on me. I have determined not to wear anything that makes me look bigger ever again.