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A pair of shoes. Possibly archaic - dates back to when a Cadillac was considered a highly desirable car.
"I couldn't get my jalopy running, so I had to take the Sears Cadillac to work"

"His dusty boots -his Sears Cadillac" - Jimi Hendrix, "Highway Chile"
by quasarmotorsports December 10, 2009
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