More than thirty years ago, I began attending prep school in the United States. Until that point, I had lived all my life in Saudi Arabia, with annual vacations outside the "magic kingdom" when all my clothes shopping was done. Because most of the other American folk in my town were of Californian or Texan origins, the prevailing style for my age group was something like surf/ skate punk. I had a pair of those black and white checked Vans sneakers that seem to be au courant today. When I showed up at Choate, I quickly learned that boat shoes and blucher moccasins were the prevailing aesthetic. Moreover, we were not permitted to wear sneakers or collarless shirts to class. Yet I wore my black and white zebra tee and checked Vans on the weekend. I've been tempted by the repeat Vans shoes (and their imitators) but am on the fence as to whether one can hit the same trend twice, without seeming dated. Opinions?