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We've compiled the dress shoes we've tried, tested, and loved over the years, as well as the dress shoes that the rest of our stylish colleagues here at Esquire endorse

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The pair had appeared on the cover of LIFE magazine two months before their wedding, in July 1953, perched on the sloping deck of a sailboat off of Cape Cod, both of them smiling, windblown, emphatically New England-y, beside the cheeky headline, Senator Kennedy Goes a-Courting. They were both from prominent, monied, influential families, and they were frequently featured, together and apart, in the society pages of major newspapers

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