John F. Kennedy’s Personal Tailor Still Plying His Trade in New York

Late president's tailor is still filling orders and making one-of-a-kind requests decades later.

May 17, 2017 5:00 am

Among the many garment and tailor shops in Midtown Manhattan, there’s a nondescript one that happened to be John F. Kennedy’s personal favorite.

And today, Kennedy’s personal tailor can still be found working out of the same shop.

Paul Winston, 78, is the outfitter behind Winston Tailors, a custom-tailoring business that was popular with the Kennedy brothers. Winston also runs Chipp Neckwear, a tie company full of high-end neckwear. John F. Kennedy became a fan of both shops while still a junior U.S. senator from Massachusetts. His younger brother Bobby also grew to be a loyal customer.

Later, Winston and his father, Sidney Winston, fitted Kennedy during his time in office. While the Winstons had a unique inside with the first family, they never let on, thinking instead it was a bit uncouth to brag.

Funeral of President John F Kennedy
Robert Kennedy and Edward Kennedy with Jacqueline Kennedy during the funeral of President John F Kennedy on november 25, 1963 in Washington DC, United States. (Keystone-France/Gamma-Keystone via Getty Images)
Gamma-Keystone via Getty Images

After John was assassinated, Bobby asked the Winstons to re-cut his brother’s inauguration suit, which was much too large for him. The younger Winston told Town & Country, that while it may have been cheaper to simply buy a new suit, the ensemble had too much sentimental importance for Bobby Kennedy.

When the younger Kennedy had his own campaign trail to travel, he frequently called upon the Winstons to dress him.

Today, in a city full of big businesses, Winston is still working his magic as one of the few remaining neighborhood tailors, dressing New Yorkers all over the Big Apple with hand-made, one-of-a-kind pieces.

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