Richard Press, grandson of J. Press’ founder and who worked at the clothier from 1959-1991, herein debuts his column for Ivy-Style.com with a look at the competition between Ivy League clothiers during the heyday.

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I remember well the Yale-Harvard weekend of 1962. It was during the time of the War Between the Tailors.

In his coverage of the annual football contest, Sports Illustrated scribe Bob Boyle reported on the presence of representatives of the New Haven Tailoring Establishment — J. Press, Fenn-Feinstein, Chipp, Arthur Rosenberg — “who make their biennial obeisance to see what the young gentlemen are wearing. By custom they do not speak to one another, and upon arrival each goes his separate way.”

Like any small industry, the world of Ivy League clothiers was small and incestuous. Some left to work for their competitors, others to start their own companies. We all knew each other and for the most part respected each other, but competition for our niche market was often fierce.

Boyle doesn’t mention Charlie Davidson of The Andover Shop, regaling Porcellians at his shop on Holyoke Street in Cambridge. A keen competitor, Charlie always kept the place loaded with heavy bolts of English woolens in every nook and cranny of the narrow quarters.

Meanwhile the New Haven schneiderei, as they would be depicted if they practiced their trade on Manhattan’s Lower East Side, are characterized sporting “alpine hats, double-breasted tweed topcoats and blue oxford shirts to offset their sallow complexions.”

Boyle continues: “Paul Press descends into the basement of J. Press, where he stands his Cambridge branch employees to a buffet luncheon of cream soda and hot pastrami imported from New Haven.”

My uncle Irving and father Paul always enforced a dictum that is set in stone: “Have nothing to do with anybody who tries to screw J. Press.” That meant anyone who “borrowed” the mailing list, copied suit patterns, or took away fitters, tailors, salesmen or — God forbid — customers.

Nevertheless, several competitors were actually born of J. Press.

After the Second World War, Lou Prager of the Princeton store and Sid Winston who showed J. Press at prep schools like Andover, Groton, St. Paul’s and Hotchkiss, started Chipp along with Jonas Arnold from our Cambridge branch.

In 1958, premier Midwestern roadshow salesman Mack Dermer and West Coast traveller Sam Kroop went out the back door to purchase the Arthur M. Rosenberg Co. Previously Dermer sold J. Press clothes retail at the LaSalle Hotel in Chicago and eight other cities on his road trips. He generated more business pushing the Ivy League Look out of a hotel showroom eight times a year than many men’s stores do in a full season on their own premises. A couple thousand postcard notices proclaim each showing at the La Salle Hotel for our Chicago list would go out, plus a rough equivalent to 25 other cities nationwide.

Arthur M. Rosenberg actually preceded my grandfather as the top custom tailor at Yale at the turn of the century. A talented cadre of needle-and-threadmen emerged from this base, including Fenn-Feinstein, White’s of New Haven, Rosenthal-Maretz, and Langrock.

Competition sometimes got personal. When I had to represent J. Press during contract talks with the Custom Tailor’s Union in New Haven at age 22, my father and uncle wouldn’t sit in the same room with Sidney Winston or Mack Dermer.

Those were the golden years of the business, but things are different now as I enjoy my own golden years.  Today I admire Paul Winston, who retains the snappy Chipp look his father nurtured, and continues the family tradition at Winston Tailors across from the Harvard Club on 44th Street.

On a more personal note, Mack Dermer’s son Peter utilized his know-how after Rosenberg’s closing by spending several years at Southwick. A couple of years ago he married my cousin and is now family. That helps salve old wounds.

We all talk to one another now. At least the ones who are still breathing. The battlefield trenches are all quiet on the western front. — 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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