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In other words, the Boy Who Wears Shorts All Winter is a highly recognizable but largely inscrutable character, and when I asked parents, teachers, child psychologists, and a former B.

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Perhaps the most important truth about boys who wear shorts all winter, though, is that they do—most of the time—eventually grow out of it.

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Tyler Wood, 31, remembers wearing shorts all winter in snowy Boulder, Colorado, as a middle-schooler.

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Description: Tyler Wood, 31, remembers wearing shorts all winter in snowy Boulder, Colorado, as a middle-schooler.

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