Golden Years: Ivy Trunk Shows During The Heyday

They never taught me how to baste a suit at Dartmouth, but I had to learn how in a hurry when Ray Jacobs got sick on the road.

“The road” was the term used to describe retail travel exhibits that fulfilled the clothing needs of Ivy grads after they left college and refused to partake in the padded shoulders or faux-Ivy enticements found on Main Street.

In 1959 Brooks Brothers, Chipp, Arthur M. Rosenberg, Fenn-Feinstein, The Andover Shop and J. Press sent dozens of salemen to more than 50 cities across the country to promote their three-button, soft-shoulder wares.

At the time, a quarter of the J. Press business came from the road, a tradition from the ’20s when the salemen, including my father, sold their wares at boarding schools including St. Paul’s, Groton, Choate, Taft and Hotchkiss. When I went for my interview at Andover the admissions officer told my father he remembered buying his first suit from him.

The southern route for J. Press was covered by Ray Jacobs, an endearing and witty raconteur who served more than a generation of loyal customers from Philadelphia to New Orleans. Once on his rounds in Washington, measuring a suit for the imperious but underwear-clad Dean Acheson in his office at the State Department, Ray was going slowly and Acheson had appointments coming. “Ray,” said Acheson, “you’ll have to hurry up before my appointment comes. It really wouldn’t do for the Secretary of State to be caught with his pants down.”

The train rides themselves held all sorts of entertainment. One time Ray grabbed Jerry Lewis in the bar on a train from Philadelphia and screamed, “You stole my act!” The repartee ended to a round of applause from the lounge car as they rolled into Penn Station.

As for myself, I was the low man on the payroll waiting to begin my six months as a private in the Army Reserve when, with two days’ notice, I was called off the bench to serve as a varsity substitute on Ray’s next  stop, Paul’s Below The Steps, a cigar store across campus at the University of Virginia.

That’s when I found out about the basted try-on for Colgate W. Darden, Jr., Dean of University of Virginia Medical School. A basted try-on prepares the needlework of a garment for sewing. I didn’t know how to read a tape measure, let alone pin a suit. Even worse, the fitting was for a white tie and tails Darden was planning to wear for a gala event at Monticello.

Ralph Chieffo, Sr. was the chief fitter and designer at J. Press’ York Street headquarters. Before his career at J. Press he operated a custom tailoring school in New Haven and wrote the textbook “How to Tailor a Custom Suit.” He quickly gave me an emergency tutorial.

Arriving late at night in a deserted Charlottesville depot, I managed to haul the merchandise trunks from the baggage car and drag them on a wagon to the hotel. Those days railroad travel was primitive in rural Virginia. The following morning I set up shop, a pop-up store that was a York Street Potemkin Village in back of the Playboy magazines and cigar humidors.

Warehouse racks and bridge tables displayed the sample inventory amid a symphony of ancient madder, Irish poplin, and stacks of English swatchbooks. Three thousand Virginians received postcard notices for the showing. The business was brisk and I acted like a seasoned pro pinning up Dean Darden. He later told Ray to send his regards to the young Mr. Press for his fluent fitting debut.

The road trip continued to the Dupont Hotel in Wilmington where I outfitted a contingency from the Dupont family on their home grounds. Fast-forward to a final port of call at the Bellevue Stratford in Philadelphia, with a late inning at the posh St. Anthony’s Club at the University of Pennsylvania.

It was the birth of a salesman. But three weeks later I was a private at Fort Dix, where my try-ons were KP and latrine duty. — RICHARD PRESS

23 Comments on "Golden Years: Ivy Trunk Shows During The Heyday"

  1. What must those Ivy Leaguers have thought of living in “San Fancisco”?

  2. Actually a pretty trad town until the Summer of Love. There are still some old-school preps, though, like a boss I worked for when I lived there. Pacific Union Club, and daily uniform of khakis, tassel loafers, pastel polo shirt with popped collar and navy blazer from Henry Poole he picked up in London. Added a cashmere v-neck in the winter. Tall, thin and tan in his ’50s, he looked terrific.

  3. Having left the Bay Area in June of 1965, before the Summer of Love, I still have fond memories of San Francisco as a trad town, light years away from L.A.

  4. again, thanks Mr Press-and when is your book coming out?

  5. Small note: it is The Hotel DuPont in Wilmington, DE, not “The DuPont Hotel.”

  6. Michael Mattis | November 15, 2011 at 2:10 pm |

    Why the quotes around San Francisco? Don’t you know what those words mean?

  7. Doing KP and latrine duty you meet a better class of people.

  8. Sorry- I assumed among this Ivy League crowd that the misspelling of San Francisco as “San Fancisco” would’ve been clear… I’m not usually a spelling dick but thought it was funny in the old published advertisement.

  9. I enjoyed this article and hope Mr Press will keep writing such
    interesting articles!

  10. Michael Mattis | November 15, 2011 at 4:09 pm |

    Robert Bain: OK, you caught me. I didn’t even notice it. But then I went to state schools!

  11. Funny- I actually went to San Fancisco State for Undergrad… I’m sure that’s why it stood out to me instantly. And as a fourth generation Northern Californian I can vouch for San Fancisco’s status as more Trad than LA, where Ed Hardy passes for dinner wear…

  12. Michael Mattis | November 15, 2011 at 6:56 pm |

    Also an SF State grad. Still live and work in The City.Trad fad is making some inroads in surprising places these days. I went flâneuring around the Mission on Sunday — a foreign country since I’m decidedly the North of Market sort — and saw quite a few examples of prepster-hipster fusion. Fred Perry polos with slim trousers are quite the thing among the “fixie bike” crowd. I even saw one young fellow wearing one with an ascot or day cravat. We’ll see how long that all lasts.

  13. I enjoyed this story tremendously and had no idea that such a large percentage of sales came from the road.

  14. GREAT STORY! I have old old press tie that lists SF as a store site- anyone know anything bout the Press store that was (?) here?
    -native frisco

  15. The J. Press store on the second floor of 411 Post Street opened in 1968 and closed in 1978 for a ten year run.

  16. Enjoy these true tales from the road. Would be interested in hearing more about Ralph Chieffo. It appears he worked for the Yale CO-OP for a time.

  17. Pale Male | July 13, 2013 at 7:57 pm |

    San Francisco in the 1950s was quite sophisticated. And Ivy/Tradly. Hitchcock made Vertigo because he wanted to film a movie set in San Francisco and searched years for an appropriate literary property.

  18. G. Bruce BOyer | November 24, 2015 at 11:33 am |

    Mr. Press continues to delight and instruct with his ongoing memoirs, an important contribution to our understanding of American clothing.

  19. Vern Trotter | February 8, 2018 at 9:55 pm |

    Brooks had the same three road salesmen for decades until they didn’t.

    Southeast and South: Mr. O’Connor.
    Midwest and Southwest: Mr. Houseknecht.
    West and West Coast: Cannot remember.

  20. René Lebenthal | June 26, 2020 at 5:25 am |

    Please go on with your beautiful illustration of the heyday era of Ivy league clothing. Thank you !!

  21. Charlottesville | June 26, 2020 at 10:32 am |

    Wonderful piece by Mr. Press. It is always a treat to read his posts, and doubly so when they include references to my hometown. Primitive or not, I would bet a considerable sum that people out here in rural Virginia dressed better then than they do these days, despite the increase in local wealth.

  22. whisikeydent | June 26, 2020 at 11:49 am |

    I wonder if Press could recreate this approach by tapping into the decidedly trad readership of a certain website.

  23. Gary Glazer | June 28, 2020 at 4:17 pm |

    Great article as usual. My first purchase from Brooks Brothers in 1962 or 1963 was from a visiting salesperson in Cleveland Ohio. I was about 12 or 13 years old and went with a classmate to the Statler Hotel at 6th and Euclid where Brooks had a suite that was filled with the most amazing display of clothing that I had ever seen. I remember to this day that I was treated like an old returning customer-none of this”How are you little man?” I picked out a tie, was billed for it and paid with paper route earnings. I still remember the experience fondly-but the tie is long gone.

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