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I am betting some of the early (before photography) first ladies may have not been as good looking, as paintings can always be done to accent the best features. Starting with Mary Todd Lincoln there is likely more realistic documentation.
Jackie Kennedy was amazing, not just looks, but well educated, honored our country, social involved and aware.
However after seeing the display in the Smithsonian on the first ladies, my vote for most HIDEOUS Inagural Ball dress is a tie between Nancy Reagan, and that beaded sequined thing, and Barbara Bush, with Hillary Clinton in second. Poor Roslyn Carter came in third with her caftan.
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