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It became a signature that transcended time, photographed flawlessly, and communicated authority without excess

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I know that if I were to purchase any of these items, I would probably only wear them a few times over a season and then they would start collecting dust in my closet

Take a cue from shorts expert Paul Mescal and opts for some high-fashion cotton boxer shorts, or go the more languorous route in leather basketball shorts, a pleated midi skirt, or some below-the-knee waders