Irving Press was an unusual boss. Not many men’s clothiers are graduates of Yale Law School and few if any hang out regularly at the Yale Club on Vanderbilt and 44th Street, that nearly three decades after his passing bestrides the flagship store of the company he once headed.
His wide interests and circle of friends ranged from golf cohorts; Yale intimates, Scottish Mill tradesmen, menswear mavens and many of the customers at J. Press whom he ended up conversing with under the bolts of woolens in his favored corner by the customs department.
Frank Sinatra’s time at J. Press in 1969 covered many visits to 16 East 44th Street, where he got to know most of the staff on a first name basis, generously signing autographs for whoever had the nerve to ask him.
Uncle Irving Press and Frank happened to bond one day after I introduced them. They engaged one another discussing Sinatra’s boyhood idol and my uncle’s classmate, singer, and entertainer Rudy Vallee. Known as “America’s Crooner” several years before Bing Crosby’s hit records and more than a decade before Sinatra’s, Vallee transferred from the University of Maine joining my uncle in the Yale Class of 1926.
The men were also members of the Yale Collegians, a band made up of students working their way through college by both playing music in the student dining hall for free meals and by taking on paying gigs at country clubs, school dances, and proms. Sinatra particularly liked Irving’s story about how, when a singing violinist didn’t work out (and they rarely do!)Vallee began singing through the same megaphone he used to project the volume of his saxophone, alongside non-singing violinist Uncle Irving, who regularly shared the stage with him.
But when Rudy packed up the Collegians (along with his degree in Philosophy) and took up residence as the house band at the Heigh-Ho Club at 35 East 53rd Street in Manhattan, neither of his two violinists was named Irving Press. It was a personnel decision that would forever alter the history of both popular music and men’s clothing.