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A Hawaiian shirt improperly worn can make you look like a middle-aged undercover cop on vacation but done right, it can teleport you to stratospheric levels of cool. This particular version, once owned by President John F. Kennedy, himself, has its place in the pantheon of ultimate tropical style. This blue shirt by Hale Hawaii that’s replete with fruit, fish, and fronds, was “loaned” to family financial advisor Thomas J. Walsh by JFK at a poolside event where Walsh wasn’t appropriately clad for the occasion. Inside the shirt is sewn a tag that reads, “John F. Kennedy” and has never been removed. There’s no word on how many Cuban cigars were smoked while JFK was wearing it, but the historic significance of this shirt cannot be understated. It’s now up for auction by Guernsey’s in New York City and is expected to fetch between $15,000 and $20,000. The winner will probably have it mounted and framed instead of wearing it to the local bar for dollar beer night.

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