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Whether you are pulling pranks in the state hospital or writing raunchy poems, this slip-on shoe (and your suave good looks) was going to get you out of a jam. With a stylish wingtip design, tough leathers, an electric blue lining, triple stitching, and a tunite sole partnering a stacked leather heel - the Orlovsky was perfect for all the semi-sincere jokesters out there (think Mentos commercial meets Swingers).

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