Ivy Style

Nobody told Frank Sinatra the heyday of Ivy was dead when he steered his entourage into J. Press on a January afternoon in 1969.

“Dressing The Chairman,” an upcoming off-Broadway play scribed by Joseph Cosgriff, tells the story of an unexpected and fascinating odyssey that began when Sinatra commanded, “Lemme see all your 38 Regulars.”

Cosgriff was my collaborator for our Amazon e-book, “Rebel Without A Suit,” a stand-alone essay from a larger book we were researching that navigated the minefields of men’s fashion. The Sinatra saga, originally a Golden Years column here at Ivy Style, was the nexus of a 30-page chapter from our unpublished book that playwright Cosgriff thought ripe for further exploitation on the stage. He is co-author of “A World On A String: A Musical Memoir” with jazz guitarist and singer John Pizzarelli, and is a personal encyclopedia of popular music and Sinatra history. Joe also wrote one of Pizzarelli’s most popular hits, “I Like Jersey Best.”

During the planning process, we engaged in numerous beers and good fellowship. I confessed to him my hope he would be able to make the stage Richard Press wittier and with more pow than the real life one. “Not a challenge,” he said.

The play’s one-man stage character, “a well-preserved man in his eighth decade, Richard Press,” is to be portrayed by a professional actor on a set depicting the main floor of J.Press’s 44th Street store as it might have looked in 1969. “Richard” takes the audience along with him on his eight-month adventure of not only pinning and chalking the singer’s suits with J.Press fitter and holocaust survivor Felix Samelson, but also being welcomed to spend time among Sinatra’s inner circle. Afternoon sessions at the Biltmore Bar, dinner at Quo Vadis, nightclub shows at the Rainbow Room and late night visits to Jilly’s and Toots Shor’s were all part of Sinatra’s Manhattan during the late ‘60s.

Stage character Richard tells the audience the what’s what of tectonic change. Imagine running an Ivy League clothing store in New York City smack dab in the middle of the Age of Aquarius. If asked to describe fashion in 1969, people often had one foot on the boat and the other on the dock. Sure there were Nehru jackets psychedelic colors, and the Fifth Dimension’s TV specials. But it was also a time when people were still wearing hats and ties and their Sunday best to the World Series. We still had our fair share of big shots who would come into our Manhattan location, and more than occasionally a famous person would jump in with both feet and announce his intention to begin a professional relationship with J.Press that would include chalk, pins, and tape measures.

Around that time our store had an enviable old-school roster of recognizable regulars: the debonair Cary Grant, Walter Matthau, author Kurt Vonnegut, playwright Edward Albee, anchorman John Chancellor and talk show host Dick Cavett.

That day in January when Sinatra got to the back of the store, he proceeded to try on a half-dozen suit jackets from the 50 or so in his size that I swung over to him on the mobile garcy rack. He was wearing a grey herringbone from Carroll & Co. of Beverly Hills. I recall him pointing at that suit and saying, “This is the kind of suit I like. See what you can do.”

Knowing what he wanted and being no stranger to a menswear store, he carefully took in all the available angles of each suit by way of the honest-but-unforgiving three-way mirror. Make no mistake, 38 Regular was Sinatra’s size. As only someone who has taken afternoon naps among racks of suits would pick up on, I swear I once heard Sinatra ad-lib that he was a 37 Regular during a radio show skit in the early 1950s. But it was now 1969, and those old Bob Hope skinny Sinatra jokes we’d hear on the radio — Hope once called him a breadstick with lungs — no longer applied to the man who was more thickset in stature as a 53-year-old. The following week, after an ever-so-slight letout by Felix, it was spot-on. The 38 was a perfect fit.

After trying on the sixth suit he took an exaggerated look of displeasure that he goosed with a well-honed comic pause. “I’ll take ’em all,” he finally said, breaking into a wide grin. “And by the way, no more ‘Mr. Sinatra.’ From now on it’s Frank, understand?”

He sealed the deal with a tweed suit. “Hey, Richie, do I look like I went to Yale?”

Ten days after the initial fittings, Team Sinatra returned to the store to reconvene for the final fittings in the midst of which he gave everybody marching orders: “Let’s get our asses out of here and over to the Biltmore Bar.” Proceedings were promptly called to order as Sinatra strode to the bar and presented himself to the bartender with the words, “Take out a couple of bottles of Jack Daniels.”

Dr. Maurice Saklad, NYU prosthodontist, was a trusted enclave crony personally available at all times to Sinatra. I knew him from having been assigned the locker next to his at my home away from home, The City Athletic Club, on 54th Street. Pulling me aside, Maury passed along some friendly but ominous advice. “Richard, all I can say is stay on your best behavior, do whatever Frank wants, don’t cross him, and you’ll be fine.”

“Um, s-s-s-sure,” I replied. It had never once occurred to me to cross Frank Sinatra, whatever that meant. But then it did soon occur to me that were I unknowingly to do so, it would probably be too late to walk it back.

Stay tuned for updates on the play. I did it his way. — RICHARD PRESS