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To mark its 75th anniversary, Sperry Top-Sider will debut its “Passion for Prep” consumer sweepstakes Tuesday, to coincide with the release of “True Prep,” a new book by Lisa Birnbach. The brand’s shoe was featured on the cover of the author’s first novel, “The Official Preppy Handbook,” published in 1980, and to commemorate the second reunion with Birnbach, Sperry is running an online photo contest where fans can upload pictures of themselves in their best preppy outfit to the brand’s website or Facebook page. Each week, the person with the winning photo will receive a pair of shoes, and one grand-prize winner will receive a vacation in Nantucket, Mass. “We hope the contest will remind our fans to keep having fun in their Sperry Top-Siders, as well as inspire a new generation of nautically minded prepsters,” said brand President Craig Reingold. Birnbach also will visit Sperry retail locations for book-signing events; the contest ends Nov. 2.