Birth of a Salesman

They never taught me how to baste a suit at Dartmouth, but I had to learn 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 refusing to partake in the padded shoulders or faux-Ivy enticements found in Middle America.

 In 1959, J. Press, Chipp, Arthur M. Rosenberg, Fenn-Feinstein, Andover Shop and Brooks Brothers sent dozens of salesmen to more than 50 cities coast to coast peddling three-button, soft-shoulder, button-down wares unavailable elsewhere.

 Nearly a quarter of the J. Press business came from roadshows, a tradition originating in the 1920s when J. Press traveling representatives, including my father Paul Press, sold their wares at fabled St. Grottlesex New England boarding schools. During my interview at Andover, the admissions officer told my dad he bought his first made-to-order suit from him his freshman year. Pre-World War II, boarding school elites didn’t buy their flannels and tweeds off the rack. I got into Andover, but my father’s real boss, eponymous Grandpa Jacobi preferred Loomis (now Loomis Chaffee) because he considered it a more democratic institution.

 The southern route for J. Press was covered by Ray Jacobs, an endearing and witty raconteur who served more than a generation of customers on his southern route 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 fostered varieties of entertainment to mitigate the boredom of a long train ride. Ray once grabbed Jerry Lewis in the bar car on a train from Philadelphia and screamed, “You stole my act!” Their vaudeville repartee ended to a round of applause from the mostly inebriated lounge car patrons as it rolled into Penn Station.

 Entering the family business after college I was low man on the payroll. Out of the blue on two days’ notice, I was called off the second team bench to fill Ray’s next stop slated for Paul’s Below The Steps, a cigar store across the street from the University of Virginia.

 I was informed I needed to perform a basted try-on for Dr. Colgate W. Darden, Jr., Dean of University of Virginia Medical School. A basted try-on prepares the needlework of a garment for sewing. I barely knew how to read a tape measure let alone pin a suit. To make matters worse, the fitting was for white tie and tails he was preparing for a gala at Thomas Jefferson’s home base in nearby Monticello.

 Ralph Chieffo, Sr. was chief fitter and designer at J. Press, York Street. Prior to his career at J. Press he operated a custom tailor academy in New Haven. The curriculum featured his iconic textbook “How to Tailor a Custom Suit.” Tailor-Professor Chieffo gave me a lightning tutorial in trench warfare real time.

 Arriving late at night to a pre-Civil War deserted Charlottesville depot, I managed to haul the weighty merchandise trunks onto a baggage cart, dragging the creaking wagon to the nearby vintage hotel. Railroad travel in 1950s rural Virginia was still Huck Finn primitive. The following morning I set up shop, a fake pop-up York Street Potemkin Village behind the tobacco stand, piles of Playboy Magazines available to peruse during slow times.

 Warehouse racks and bridge tables displayed a random sample inventory amidst a symphony of Irish poplin ties next to books of English mill fabric samples, button-down shirts, Argyle socks, cotton Oxford drawers, the whole schmear.

 Three thousand Cavaliers received postcard notices announcing the showing. Business was brisk. I fulfilled my fitter obligation pinning and chalking Doc Darden like a Savile Row veteran. He later told Ray to thank “young Mr. Press” for his fluent fitting.

 The road trip continued to the Hotel Dupont in Wilmington serving a contingent from the Dupont family on their home grounds. Fast-forward to final port of call at the Bellevue Stratford Hotel in Philadelphia with a late inning bash at posh St. Anthony’s Club attended by J. Press wannabes from the University of Pennsylvania.

 My birth of a salesman worked better for me than Death of a Salesman for Willy Loman. Three weeks after the roadshow terminated I was serving Uncle Sam in basic training at Fort Dix, New Jersey. Private Press’ try-ons now included peeling KP potatoes and scrubbing toilets on latrine duty.








You will always be Dick to me. I still remember that you were the best dressed and funniest person at the Chi Phi House. I am gland whoever owns J. Press now still keeps you as the front person for the company.


Peter McCrea May 04, 2020

Speaking of trunk shows, here is an entry I submitted a few years ago to the Bulwer-Lytton Bad Writing Contest:
“OK, you scurvy lousy rebels”, Brooks shouted, “It’s time for a necktie party!”, as his brothers rounded up the ill-dressed and uncouth strangers and marched them to the dusty town square where they were having a big trunk show with stripes, repps, paisleys, foulards, polka-dots, and neats.

Dave Nelson April 15, 2020

I attended the University of Virginia in the late fifties and early sixties when Colgate Darden was the President. Dean of Students was B. F. D. Runk.
Charlie Hotchkiss
April 14, 2020

Charlie Hotchkiss April 14, 2020

Delighted with Dr. Darden’s upgrade.

Richard E. Press April 14, 2020

Many fond memories of Ray Jacobs at the Bellevue Stratford in Philadelphia. The era: 1948 – 1952.

William A Kattermann April 13, 2020

This is a great story. Colgate Darden, however, was the president of UVa, a former governor of Virginia, and an attorney (not physician). Decades earlier, he married a duPont. This makes Richard’s trip from Charlottesville to Wilmington even more significant.

Christopher Bright April 13, 2020

I went to Virginia in the mid-sixties and remember the rather elfin Ray Jacobs well. I was a good customer and he took excellent care of me, fitting me with fine tweed jackets and custom linen suits. While the estimable Mr Press’s recollection of Paul’s is exactly right, I must take issue with one point. Colgate Darden was President of the University of Virginia, not dean of the medical school. Mr Darden, the former Governor of the Commonwealth, was a lawyer by training and profession.

Ralph Hardy April 13, 2020

And I thought having custom dress shirts made from J.Press was incredible-
What a world of custom suiting that was!
Thank you for my continuing haberdashery education !

Patrick Simmons Harrigan April 13, 2020


Thanks for sharing this rich history chapter of J. Press!

Michael Smith
CEO The Custom Shop Clothiers

Michael Smith April 13, 2020

And who was the outstanding Midwest rep-Peter? A wonderful person with lots of tweeds and corduroys to sell to Press fans in what one author called the heart of the heart of the country….

Warren VanderHill April 13, 2020

My brother and I used to go to the old Tutwiler Hotel in downtown Birmingham, Alabama, in the 1950’s and 1960’s, twice a year to visit the J. Press traveling salesman, “The Venerable and affable, Ray Jacobs”, to order our Spring clothing in the Fall and again in the Spring to order our Fall clothing. It was such a treat to go and see the new clothing lines and get to spend time with Ray Jacobs! I miss those days and the simplicity of authentic men’s clothing from J. Press. I always loved hearing the stories of the “Road” from Ray!

Thank you for sharing this wonderful story and tribute to the bygone days of fun laughter and quality American Clothing brought to us by your “Roadies” and in particular, Ray Jacobs! With my greatest respect to you and your company, Preston Goldfarb

Preston Goldfarb April 13, 2020

“Bringing the store to you” is the highest order of haberdashery, The trunk show of Nettleton shoes at Gordons, Ltd. in Greensboro carries on the tradition!

Robert W. Emmaus April 13, 2020

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