“My father always used to say we’re in the ‘want’ business, not the ‘need’ business,” 78-year-old Paul Winston said on a recent afternoon in his midtown Manhattan office, cracking a smile. Winston runs the tie company Chipp Neckwear, as well as Winston Tailors, a custom-tailoring business known for its traditional Anglo-American style.

One fan of those Ivy League-inspired roots was John F. Kennedy, who became a Chipp customer when his brother-in-law, Peter Lawford, brought him into the shop one day in 1958 when Kennedy was still a junior United States senator from Massachusetts. Lawford had been having Chipp make his clothes for his television show The Thin Man. Bobby Kennedy soon became a customer as well. For the duration of JFK's presidency, from 1961 to 1963, Paul and his father attended to Kennedy and did bespoke suit fittings at his private apartment at the Carlyle Hotel.

Sidney Winston, Paul’s father, had known the Kennedy boys since their prep school days; before he started Chipp in 1945, Sidney worked on the New England boarding school trunk show circuit as a travelling salesman for J. Press. It was during this time that he also met future IBM Presidents Tom and Arthur Watson, as well as Cyrus Vance Sr., all of whom became some of Chipp’s biggest clients over the next several decades.

Bobby and Jack Kennedy at the White House Getty/Bettman Collection

Paul Winston had a unique view inside Kennedy's short presidency. On one occasion, Bobby and Jack were picking out suiting fabrics in the Oval Office while images of troops being sent to desegregate schools flashed across the television. Paul also recalled meeting Kennedy in the living room of his Carlyle apartment in 1962 when he was clad only in his back brace and a pair of boxer shorts. JFK suffered from chronic back pain throughout his life, and wore the brace over his shirt. His suits needed to be fit specially to accommodate the brace and he almost always kept both buttons of his jacket done up to conceal it. (Many thought the buttoning of both jacket buttons was merely a sartorial faux pas.)

The Winstons never let anyone know that they made clothes for the president. As proud as he was, Sidney Winston believed that taking any photos with the president would have been crass, just as revealing their role as the president’s tailors to the newspapers would have been. He didn’t mind when that the press reported that that other tailors like Brooks Brothers or H. Harris made the president’s clothing.

Paul Winston in his midtown Manhattan showroom Al Castiel III

After JFK’s assassination, Bobby Kennedy called on Chipp to re-cut his brother’s inauguration suit to fit him, as they were entirely different sizes. This process was far more expensive than having a new custom suit made, but Paul believes that Bobby wanted it done for sentimental reasons. During his presidential campaign, RFK met frequently with Sidney and Paul Winston for new clothes, since they were constantly being torn off him by overzealous crowds along the campaign trail.

Today, the Winstons run a thriving tie business. They're known for their affordable knit and grenadine ties, as well as club ties with humorous messages and ones adorned with dogs of almost every breed imaginable—all made in New York. Paul considers himself mostly out of the retail business these days, but he still makes made-to-measure and fully bespoke clothing for clients.

The Winston tailors customer, Paul says, is “a guy that likes clothes.” All of his garments are made by hand in the U.S. His house style is a darted, three-button (that rolls to the second button), natural-shouldered jacket, but they are always willing to accommodate even the most radical styling requests. Some customers opt for bold, one-of-a-kind linings that Winston has made in Italy on luxurious silk.

In addition to its association with the Kennedy family, Chipp also has ties (no pun intended) to New York’s famed 21 Club. Peter Kriendler, the restaurant’s former proprietor (whose uncle Jack Kriendler was the founder), was a longtime Chipp customer. The restaurant has always required patrons to wear a jacket, and throughout the 60s, the loaner blazers, in a range of sizes, along with neckties, were all from Chipp.

Paul Winston recalls fitting JFK for clothing at his private Carlyle Hotel apartment. Getty Images

Winston Tailors is located at 28 West 44th Street in New York City. It is open by appointment only and can be reached at 212-687-0850.

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