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Dressed like your right out of a J.Crew or [Banana Republic] catalog. It differs slightly from 'J.Crew' or Preppy in that it's a phrase applied to a situation where the clothes are wearing the man rather than a [particular] lifestyle reflected in the clothes worn by the man. For example: a medical tech who usually wears blue hospital scrubs dressed in chinos and a button-down plaid shirt; all creases were crisp (right out of the package)...or... A a slovenly overweight college kid raised by Vermont hippies and who's never worn a tie, dresses to meet his [girlfriends] parents.
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