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In the 1940s, Dorothy Merley arrives in a snowstorm to meet a mysterious man named William -- a man who employs her to write a very important letter to FDR. William gives Dorothy a pair of galoshes to keep her feet warm. In this anthology film, we trace those shoes over 13 decades, into the future year of 2071, to see stories from the lives of the people who owned and wore this pair of galoshes, passed down for generations.