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Jennifer Connelly in the movie, "Seven Minutes in Heaven", Anne Twomey in "Deadly Friend", which also starred Kristy Swanson, who wore penny loafers in "Dream Trap,"; Sharee J. Wilson wore them in "Crimewave", Meg Ryan in "When Harry Met Sally", Kim Basinger in "The Real McCoy", Mary Stuart Masterson in "Married to It", Barbara Hershey in "Hoosiers", Cheryl Waters in "Macon County Line", also Sarah Berry in "Evil Dead 2", Gwyneth Paltrow in "The Royal Tennenbaums"; if I can think of any more, I'll add on at a later time.

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Q: What celebrities wore Penny loafers?
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They call Penny Loafers Penny Loafers because they are loafers in you put pennys in them


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