Golden Years: My Brief Bromance With Frank Sinatra


Note: This column originally ran on January 22, 2013, and is being reposted today following news of the death of Sinatra’s wife Barbara Sinatra at age 90.

* * *

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 1969. 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

39 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.

  16. G. Bruce BOyer | December 12, 2015 at 11:38 am |

    Another wonderful and wonderfully told story from Mr. Press. A good place to see Sinatra in his Ivy period togs — including sports jackets, suits, and tuxedos — is in the 1960s “A Man and His Music” specials that he made for TV. What’s fascinating for me is that, at least in this instance, he bought off-the-rack rather than custom. Thank you again Richard Press.

  17. I like his work, both in song and film, but from what I’ve read about daily life with F.S., I just don’t think I would have enjoyed being around him. Stories abound of his demeanor and “stunts” at places like Chasen’s, and a jerk is a jerk, regardless of fame, fortune, or feather. I’ll never know for sure, of course, but I’m confident that I’ll lose zero sleep over it, too. First person stories are always interesting, though, and I’m glad to add another to the list for this guy. Thanks for sharing, Mr. P.

  18. We live in an era in which it’s difficult to appreciate the art, political accomplishments, etc. of people, usually dead white males, who have character flaws of any kind.

    Just last night I was in conversation with a woman of the Millennial generation, and when Sinatra came up in an offhand remark (we were talking about French cabaret music and I mentioned Charles Trenet, calling him “a kind of French Frank Sinatra” [perhaps not an accurate comparison]), she immediately said that she didn’t like Sinatra. When probed, she called him something along the lines of a jerk and womanizer. Then she added the same problems make JFK “problematic,” a popular epithet for those under 25.

    Going forward, anyone aspiring to be a public figure should expect to not only have talent, but be a model citizen.

  19. Ward Wickers, FIFS | December 13, 2015 at 10:52 am |

    “Going forward, anyone aspiring to be a public figure should expect to not only have talent, but be a model citizen.”

    Like Donald Trump, you mean?

    This is a great story. I view Sinatra, along with Nat King Cole, as the best male vocalists I’ve ever heard.

    Reading this, I found myself trying to imagine what it must have been like to have Sinatra and his entourage come into the shop and see Joe Fish. That probably would have taken my breath away, as I assume he was a known mafioso at the time. I would have been thinking (if I were Mr. Press), “What is he going to do with his gun when trying on suits?”

  20. But Trump is compared to Hitler in the media.

    If you don’t want to be compared to Hitler in the media, you’d better be a model citizen.

  21. @Mark Seitelman
    I think it’s safe to say that Frank loved his duds. Legend has it that when a Speaker of the House once placed an arm around his shoulder he was rebuked with “hands off the threads, creep!” Not exactly pleasant, but a means of making one’s fondness for one’s threads immediately felt.
    And, once more, thanks are roundly due to Richard Press for a thoroughly splendid piece.

  22. One Note Samba is a gem.

  23. Ward Wickers, FIFS | December 13, 2015 at 1:28 pm |

    It is a great bossa nova gem. Many of Jobim’s songs are gems.

  24. Bags' Groove | December 13, 2015 at 5:03 pm |

    One Note Samba is unquestionably one of the greatest bossa nova compositions, but it failed to feature among the ten tracks of the brilliant Francis Albert Sinatra and Antonio Carlos Jobim, turning up as one of seven Jobim tracks on one half of Sinatra & Company.
    Sinatra and Jobim, musical geniuses both.
    But my all time favourite interpretation of One Note is that of Stan Getz and Charlie Byrd. Eternal.

  25. Per James Kaplan’s new very good and very long bio of The Chairman the “take your hands off the suit creep” may be apocryphal. On the other hand Frank’s explanation of Strangers in the Night can’t be repeated. The suits and jackets from the early sixties are tres Ivy and the specials demonstrate how timeless they were relative to ones worn in the seventies. As to music the Cole Porter and Jobim are sublime but never overlook Moonlight in Vermont.

  26. Ward Wickers, FIFS | December 13, 2015 at 8:50 pm |
  27. Wonderful video. Artists are usually remembered for their records, but YouTube has provided the means to appreciate all of the spectacular renditions from live performances and TV shows, otherwise forgotten.

    And I just realized my family has its own Sinatra anecdote.

    When my mother was in college, she and a girlfriend spent the weekend in Reno. They were leaning on a railing overlooking the casino, when Sinatra and Buddy Greco came up the stairs. The men flagrantly checked my mother out, to the degree that Sinatra stumbled on the top step.

    I discovered him senior year in high school when I started listening to oldies on AM radio. Then I started buying his records at the used record store, because they were so cheap and had such cool covers.

    I converted them to cassette tape, and when I graduated, my parents gave me some money for my first solo road trip down to Hollywood and Beverly Hills. The first night I tried to find a camp site to save money, but it didn’t work out and I ended up just taking a sleeping bag and plopping on the beach in Santa Barbara. It didn’t go very well. The sand was uneven, murder on the back, the ocean was tumultuously noisy and I was assaulted by sand fleas.

    At 4 AM I gave up and decided to just drive the rest of the way to LA. I’ll never forget the next couple of hours as they were one of those crystallized moments when everything falls vividly into place and you’re really living in the moment. I’m driving our pickup truck down Pacific Coast Highway, the road is desolate, and dawn is just breaking, the light hitting the Pacific Ocean. Sinatra is singing poignant, Capitol/Nelson Riddle-era ballads like “Angel Eyes” and “Put All Your Dreams Away.” The adventure of life lay before me.

  28. Henry Contestwinner | December 14, 2015 at 12:22 am |

    Trump, a populist, is being demonized because he isn’t a liberal. On the other hand, Hillary, who appears to have let Americans die, seems to have violated numerous laws, and possibly even committed some felonies, is given a pass by everyone—except for a few members of the same “vast, right-wing conspiracy” that shamelessly persecuted her philandering husband, the disbarred lawyer & alleged rapist.

  29. Ward Wickers, FIFS | December 14, 2015 at 9:06 am |

    “Wonderful video. Artists are usually remembered for their records, but YouTube has provided the means to appreciate all of the spectacular renditions from live performances and TV shows, otherwise forgotten.”

    Frank and Ella are two of my favorite singers of the Great American Songbook. I have Sirius in my car and they have a Sinatra station. They play lots of Sinatra, of course, but also other great singers of the American Songbook. Nancy and Tina — Frank’s daughters — often host segments, telling stories of their father, his relationship with other singers (especially Dean Martin), and other interesting anecdotes. Nancy once mentioned that Frank was a huge fan of Ella and her work. She said he regretted not making an album with her. You can see from that old video it would have been one helluva album. Fortunately, we do have that.

  30. Ward Wickers, FIFS | December 14, 2015 at 9:28 am |


    Good story about driving to LA. I know about sleeping on the beach with sand fleas …

    My boyhood friend’s family owned a cottage on Long Island Sound (where I learned about sand fleas). In the summer of 1968, I was a young adolescent, but recall vividly the riots that were occurring in New Haven. We were at my friend’s cottage, which wasn’t too far from the city. All the talk was about the riots, how bad they were, were they going to come here, etc. — all the crazy kind of chatter that people engage in when afraid.

    It was especially hot that summer and air conditioners weren’t widely available yet (probably part of the reason why the folks in the inner city were rioting). Every nearby cottage had their windows open to catch a little sea breeze, despite the fears that the riots might be coming down the road. One neighbor was playing a Sinatra album, and we could hear it’s melodies wafting over the fearful chatter. It wasn’t long before the people around me had quieted their talk of riots and, almost subconsciously, moved over beneath the window of the neighboring cottage (you could do that then without fear of being arrested). “Come Fly With Me” and a few other songs changed the group’s psychology. When the album was over, people decided it was time to go home and did. It was the first time I witnessed how powerful music can be.

  31. He was a serious man–by temperament and interests. Especially the older version. I forget where I read this, but I recall a remembrance that, while cleverness and sarcasm and irony weren’t lost on him, he had no taste for them. And it’s easy to forget that the Rat Pack, at first deemed a stroke of marketing/publicizing genius, died following a relatively short life. It became silly, and I think Sinatra, at heart, wasn’t a silly man.

    He would be so out of place these days–the current vibe. I suspect he’d retain a good bit of contempt for Stewart and Colbert and other outposts of irony and practitioners of the lighting fast bon mot. I canrelate. About 90% of what I’m supposed to find funny…I don’t find funny. (This is particularly true of Peter Sagal’s “Wait, Wait, Don’t tell me…” That has to be a laugh track, right?).

    I’ll take the older Sinatra any day of the week.

  32. @Christian

    Would you agree that when a politician is compared to Adolf Hitler, the person making the claim seldom has much with which to back the comparison?

    @Henry Contestwinner

    Oh, come on man. Trump is a vindictive little man with years of evidence to back it up. The media’s numerous passes to Hillary Clinton are as obvious as grass being green.

    Regarding Sinatra, his album with Count Basie, to me, ranks the highest. Fly me to the moon, of course, is great. My favorite from the album is Wives and Lovers. Sinatra’s voice, Basie’s arrangement and fantastically politically incorrect lyrics. “Day after day there are girls at the office, and men will always be men. Don’t send him off with your hair still in curlers, you may not see him again.”

    Kick your shoes off baby!


  33. Henry Contestwinner | December 15, 2015 at 12:28 pm |

    sacksuit, I’m not a Trump fan, but Christian has a point: Trump is being likened to Hitler, which is far worse than he deserves, even if he is “a vindictive little man” (which I haven’t really seen, but perhaps I haven’t looked closely enough).

    Both Trump and Carson are existential threats to the status quo, and both are doing well—at this point. Who knows what next year will bring?

  34. @Henry

    Nor am I a fan of Trump’s. He himself has said repeatedly that he has a long memory (probably the longest and the best) and that he holds grudges (probably the strongest and best as well). I think it would not be too much of a stretch to assume that he would wield great power in a way that would crush his enemies, both real and perceived. It would not be difficult to imagine an instance in which he would use imminent domain to persuade or ruin an individual or a larger segment of the population.

    I believe the press is nothing more than lazy when they compare Trump to Hitler. They seek to evoke a visceral response from the people foolish enough to believe them. Trump does not seek a final solution to the Jewish question, but I believe he has a great deal in common with the most liberal candidates from both parties. Many of them have socialist leanings and Hitler was a socialist. Just saying.

    I think that Trump is far from being a threat to the status quo, rather he is the status quo on steroids.

    I’m afraid I will have to remove my Carson bumper sticker from the back window of my car soon. It will be replaced with one for Cruz.

    I have seen Cruz wearing some snappy clothes and he is an Ivy Leaguer. Time will tell.


  35. The Trump/Hitler comparison is pretty lazy, and historically inaccurate.

    But there is a much more apt analogy to be made. Trump today is playing a role in politics quite a bit like that played by Henry Ford in the ’30s.

  36. The Trump/Hitler is accurate. Hitler killed millions of people he didn’t like/ Trump says nasty things to people he doesn’t like. 😉

    Cruz 2016

  37. So Sinatra is Ivy style’s and Press’s connection to the made men hanging out at the old Northeast Kansas City Men’ Democratic Club ot the Cigar Box or Legs Gentlemen’s Club? Not to mention Gucci bit loafers. 😉

    Just ribbing ya, Merry Christmas and Hanukkah to all.

  38. Never too late for correction: he asked Vida and Richie to meet him at Quo Vadis on 63rd Street between Park and Madison Avenue, one of the swankiest and most popular restaurants of its era in Manhattan.

  39. Ken Barber | July 26, 2017 at 10:12 am |

    Interesting that things said above about Trump in 2015 are truer today.

1 Trackbacks & Pingbacks

Comments are closed.