My Year Dressing Frank Sinatra

The current New York City pandemic way of life featuring an empty Yankee Stadium and vacant indoor dining brings me back to another place and time.

There was no pandemic slack on 44th Street in mid-January of 1969.

J. Press enjoyed a hard-earned reputation for quality, ensuring visits from New York celebrities – actors, entertainers, athletes, writers, and business executives. But things changed in a hurry when a familiar face entered the store and simply said to me, “Show me all your 38 regulars.” Our visitor was Frank Sinatra.

Thus, began my eight-month odyssey of dressing Frank Sinatra, a job I soon learned came with pressure, responsibilities, and expectations. More than overseeing pinning and chalking the suits, pants, and sport coats, I quickly attained borderline insider status and was soon joining Sinatra’s travel team for Jack Daniels at the Biltmore Bar, dinner at swank restaurant Quo Vadis, and late-night drinks at Toots Shor’s and Jilly’s. There was also a memorable night at the Rainbow Room for a Frank Sinatra, Jr. performance where wife Vida and I basked in the glow of the standing ovation that greeted the entrance of the elder Sinatra and his party as we walked to our table.

Sinatra’s generosity extended to his friends and he bought new suits at J. Press for an A-list entourage of legendary chums – Academy Award-winning composer Jimmy Van Heusen, noted saloon keeper and sometime-bodyguard Jilly Rizzo, and reputed mobster Joe (“Joe Fish”) Fischetti.

The adventure came to an end when the phone rang making the dénouement official - after about two dozen suits, a full collection of sport coats, everything orange that was manufactured by J. Press, and memories that would last a lifetime, Sinatra ended the relationship. And as he had done with Lauren Bacall, Mia Farrow, and likely with many other players in his personal and professional life, he outsourced the breakup to someone else.

Among the stammering words delivered by the young Warner Bros. flack assigned to the task of firing Richard and J. Press, “Mr. Sinatra has decided to move on” slammed the door with surgical finality. The inevitability of the soap opera ending did not soften the sting as the entire J. Press gang collectively brooded for weeks, not unlike characters in a Sinatra saloon song.

It turned out 1969 was the time Frank Sinatra broke up with New York City, a place he’d visit often (and famously sing about ten years later) but never again consider home. It was a time when the bartenders were the celebrities. Maybe this was what he was thinking when he discussed with me the prospect of moving full-time to California. It was a time New York was defined as much by its saloons, gin-joints and night clubs as it was by Broadway plays, Carnegie Hall and Wall Street.

Years later, my son Ben, serving a political internship at the 1989 George H.W. Bush pre-inauguration gala, was assigned to “cover” Frank Sinatra prior to his onstage performance. When Ben introduced himself Sinatra responded, “Oh my God, how are Vida and Richie.” Yep, he remembered our names.

Sinatra fed Ben his memories of his time at J. Press. "I’ll never forget Felix the fitter filling me in about his time at Auschwitz. Is he still going strong? What he did for all my blazers and my favorite tan gab suit only a genius could do. And I had a great time knocking down Jack Daniels with your dad.”

Frank told my son, “I loved doing Ivy, but felt it was time to move on. Give the J. Press gang, your mom and dad my best.”

More than half a century later, it all worked out – the story endures.

They cant take that away from me







This is a great story — but where did Sinatra go after he left J Press???—- and i was delighted to be reminded of Jerry Haber, who took
good care of me for more than 25 years until
he retired. He corralled me one day while having a smoke outside the 44th St store and promptly sold me a sport jacket that he said was one of Mr. Press’s favorite patterns and was going fast. I later saw the same jacket on Henry Cooper of the New Yorker and John Chancellor, at the Century. We loved the jacket and the salesmanship. And I still have it 40 years later.

bob semple 8月 18, 2020

This is a wonderful story, expertly told by Richard Press. My late father, Jerry Haber, a Hall of Fame J. Press Salesman, was an avid Frank Sinatra fan and he would have loved it.

Jeffrey Haber 8月 11, 2020

Thank you for sharing your gift for narration and at a deeper level, a good hand at writing cultural history. I look forward to each installment.

Virgil Evans 8月 11, 2020

Richard and Friends ~ My intro to J. Press was via the St. Grottlesex mafia, although I had the privilege of graduating from a school very much on the periphery of that ethic. Through more than 50 years as a naval officer and a diplomat, J. Press has been a wardrob staple and has never let me down. Your product is timeless and, in my opinion, so needed in today’s virtually standard-less society. In Churchill’s words, “Never give up. Never, never, never…” Please keep it going, without apology…

Peter Thompson 8月 11, 2020

Great stories as usual. I still have a hard time imagining Frank Sinatra wearing J press clothing. I’m sure he looked quite sophisticated and charming. But I picture him more of the rat pack style

Howard Goldstein 8月 11, 2020

Thoroughly enjoy your stories. Quickly brings me back to a exciting saga in my life.

Henry Sherman 8月 10, 2020

The Chairman of the Board. I would have loved to have joined you all for Jack and stories. Amazing! Great bio on Netflix about Mr. Sinatra, by the way.

William 8月 10, 2020

Very well written piece of history. Mr. Press at York Street in the 1970’s told me I was the perfect J. Press 38 regular. But not anymore.

William J Feltus 8月 10, 2020

Thanks for a great ancedote.

Ted Schofner 8月 10, 2020

Great story and great timing. I am currently watching the Sinatra series on Netflix.

Gil Kessler 8月 10, 2020

These continual stories are great! Thank you. I guess 1969 was a time that southern California style of clothing was a changer.

Sims Harrigan 8月 10, 2020

Wow, great story!

Jay 8月 10, 2020

That is a good one…

Jim Pierce 8月 10, 2020

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