Golden Years: My Brief Bromance With Frank Sinatra

The life that late I led in the heyday was “Mad Men” in real time. Until the 1950s, retailers respected the privacy of their celebrity clientele. I played by the rules, and the paparazzi never discovered my bromance with Ol’ Blue Eyes.

Frank Sinatra walked into J. Press on a quiet weekday in 1968. I proffered my usual greeting, “Hi, Dick Press, how may we help you?”

“Lemme see the 38 regulars,” he said.

I took him to the back of the store and he tried on half a dozen suits. He carefully took in every angle from the unforgiving three-way mirror. Then, with a well timed stage pause, Sinatra broke into a grin, slapped me on the shoulder, and said, “I’ll take ’em all.”

Sinatra’s retinue included saloon keeper Jilly Rizzo, songwriter Jimmy Van Heusen, Joe Fish (one of the Fishetti Brothers from Chicago who fronted the Fontainebleau Hotel in Miami Beach), his investment advisor from Allen & Company, and his dentist, an oral surgeon from NYU who had the locker next to mine at the City Athletic Club. Sinatra selected a complete outfit for each of them.

Suited up and standing outside the fitting room in their Cambridge grey herringbone worsteds, they looked like they were going to chapel at Groton.

A few days later, Felix Samelson, the J. Press fitter, was chalking and pinning everybody. After half an hour, Sinatra called out, “Let’s get the hell out of here and go to the Biltmore.” The Biltmore Hotel, with its famous clock and glorious dark wood bar, was the favored gathering place for Ivy Leaguers. Three o’clock on a Tuesday afternoon the bar was a morgue, and it never knew what hit it. Soon Sinatra had the Jack Daniels flowing in a tsunami.

“Richie,” he said to me, “maybe you and your gal meet me at the Colony Club Friday for dinner then we’ll go see Frank Jr. at The Rainbow Room. Hey, maybe you can get a table for the J. Press gang.” That’s right, I had to fill the room for Frank Jr.

Sinatra made many more trips to the store. He knew everybody on a first-name basis and graciously signed autographs. Much more Jack Daniels flowed at the Biltmore, Toots Shor, and even his place at the Waldorf Towers.

Then I got a phone call. “Mr. Press, this is Mr. Sinatra’s assistant. Frank wants you to know how much he enjoyed your friendship, the clothes and all the kindness you have showed him, but he feels it’s time to move on.”

Ah, well. It was a very good year. — RICHARD PRESS

15 Comments on "Golden Years: My Brief Bromance With Frank Sinatra"

  1. Welcome, back, Mr. Press! You will certainly remember that “Meet me under the clock at the Biltmore” was an often-heard phrase in New York, until the demise of that great hotel in 1981.

  2. Interesting timing with this post; I just watched “Lady in Cement” (1968) last weekend on YouTube. It was the second outing of Frank Sinatra as private eye Tony Rome and also featured Dan Blocker and Raquel Welch. A club in the film is called “Jilly’s South.”

    Frank’s ventless 2-button suits are not unadulterated Ivy, but are similarly cut (at least they appear to be; he never buttons the jackets) and there are lots of OCBDs to go around as well as a few tab collars. Although made in ’68, the same year Frank walked into J. Press, for the most part the attire in the film has more of a classic 1965 look.

  3. I thought that the Sinatra’s tailor was Sy Devore!

  4. great story Mr.Press.
    thanks for sharing

  5. Several “Frank Sinatra” edition early 80’s Chrysler Imperials have been on Ebay lately. Two doors with the sporty bustleback and hidden headlights, these are sharp cars. Obviously not popular and very rare, I’ve never seen one in person.

    From what I’ve read, he and Iococca were buddies, and Lee supplied him with new cars.

  6. Keep the stories coming Richie! Loved it! Or as Ole Blue eyes would say, “Ring-a-ding!!”. Thanks for sharing.

  7. Philly Trad | January 22, 2013 at 8:34 pm |

    Frankie may have felt that it was “time to move on”, but after nearly 50 years of shopping at J. Press, I still don’t feel that way. In fact, I’m thankful that I can still find all of the basics there. I must admit, however, that I occasionaly visit Brooks Brothers for a necktie.

  8. Such an excellent article, although I never thought I would see Mr. Press using the word “bromance”.

  9. @Wriggles:

    You can only see a person in person, not a Chrysler Imperial.
    That is, “in person” refers to the object, not the subject.
    For example, in the sentence “Mr. Press saw Sinatra in person”, the expression “in person” refers to Sinatra, not to Mr. Press.

  10. I never read that Sinatra was a J. Press customer. I can picture George H.W. Bush in J. Press, but Frankie?

    I read that Sinatra purchased clothes from various Savile Row tailors.

    I also read that Sinatra loved clothes. His mother had him very well dressed, and as a youth he was nicknamed “Slacksey O’Brien.” “Slacksey” referred to his numerous outfits including slacks. “O’Brien” referred to his old man’s saloon called “Marty O’Brien”. The Sinatra’s were 100% Italian, but his father named the bar “O’Brien” in that the Irish were more established and more accepted in 1920’s and 1930’s Hoboken than the Italians. The Italians were the new kids on the block.

    But, I digress.

    I could see Sinatra as a Hickey Freeman customer in the 1960’s as evidenced by his 1963 film, “Come Blow Your Horn.”

    In the film Sinatra takes his little brother shopping on Madison Avenue. The kid brother is transformed from a Yonkers momma’s boy to a card-carrying Rat Packer. The clothing? Hickey Freeman. The young brother walks out of the store wearing a new flight coat, one of the Hickey Freeman’s signature garments. The store has a Hickey Freeman sign.

    On a side note the shopping scene has no dialogue. The soundtrack is Sinatra singing the title song. Although there was location shooting on Madison when Sinatra and brother cross the street, the clothing store is on a sound stage. On another note, the manager of the store is Grady Sutton, W.C. Field’s foil from “The Bank Dick.”

  11. Another celebrity, and a bit more of a favorite, is Dick Cavett. I’ve seen a few of the incredible interview shows from the early 70s and not a few of them advertise “Mr. Cavett’s wardrobe curtesy of J. Press” or some such. I would enjoy reading that story.

  12. I think you escaped—or, more properly, were allowed to escape—before the infamous Sinatra touch corrupted you. I have heard tales of how those around him suffered, and I am glad that you were not among them.

    Regardless, thank you for the wonderful story.

  13. I’m confused. When Frank’s assistant says, it’s time to “move on”, does that mean he moves to a different suit manufacturer? Or, is he at the twilight of his life and not long for this world?

  14. This all occurred in 1968. He still had many good years to go. Meant he was taking his clothing business elsewhere.

  15. Slacksie Polaski | April 9, 2014 at 1:04 am |

    Clifford: Really? Seriously? In 1968, this was. You idiot.

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