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

Richard Press is the grandson of J. Press founder Jacobi Press. A graduate of Dartmouth, he worked at the family business from 1959-1991, ultimately serving as president. He also spent four years as president and CEO of FR Tripler. He lives in Connecticut.

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