In 1954, LIFE Magazine declared New Haven the home of the Ivy League Look, writing “Sometimes regarded as more of a club than a clothes shop, J. Press is delighted rather than dismayed that its look is now capturing the country.”

Though it is closely associated with Old Blue, J. Press was hardly the only purveyor of collegiate clothing surrounding the Yale campus.

Retail fashion was sparse when David T. Langrock first opened his shop in a mock Tudor building on the central corner of York and Elm. Mr. Langrock, an enterprising retailer, was also a savvy real estate operator. The majestic Sterling Memorial Library was built on land he had acquired and which he subsequently sold to Yale. Langrock’s in 1950 had branches in Providence, Boston, New York and Washington DC, but when the lights of Ivy began to dim, closed its branches and left New Haven to concentrate on its still thriving store on Nassau Street in Princeton.

Arthur M. Rosenberg started his custom tailor shop in 1898. Within a few years he gauged campus style trends and shrewdly adapted the popular Brooks Brothers’ No. 1 Sack Suit to the original boxy Rosenberg pattern. He relentlessly gathered a talented sales and tailoring staff and bought adjacent buildings on Chapel Street to support workrooms for more than 50 journeymen tailors.

By The Roaring Twenties “Rosey” was the foremost custom clothier in New Haven and the largest producer of custom tailored clothing in the United States. The fact that Jacobi Press finally caught up with him by the late 1930s was perhaps reflected by my grandfather’s election as President of the Custom Tailor’s Association of America.

Langrock, Rosenberg and Press each taught their staffs to drape their clients in the right District Check and chat with them in Locust Valley Lockjaw. Sometimes it even required a change of name. Leonard Levine became Leonard Lisle, as if he were type of hosiery.

Jack Feinstein and his brother Bill Fenn were stars at Langrock when they departed to found Fenn-Feinstein in the early ’30s. They were a good cop/bad cop routine: Jack Feinstein was blustery and gregarious, while Bill Fenn projected Old Money. The brothers received a transcendent gift from their largest customer, Henry Ford II, who bought tons of clothes from the Feinsteins that matched both his physical girth and his personal wealth.

Ford prematurely gained control of the family business after the untimely death of his father Edsel. Hank, as he was called by the local trade, attempted to redress the grievance caused by his grandfather’s virulent antisemitism by awarding many new postwar Lincoln-Mercury dealerships to Jewish businessmen. The Feinstein brothers got the one on Whalley Avenue.

In 1936, Izzy White was an off-the-rack gamechanger. His son Alan — now 82 — followed his father’s stewardship at White’s of New Haven and recently shared a cornucopia of recollections with me.

The big boys were all custom tailors, and his father recognized that a vacuum existed in readymade clothing. White approached Hickey Freeman, the manufacturer of America’s most respected line of upscale clothing. Handsewn in its Rochester factory, its prime customer FR Tripler was the showcase for the company in New York. Joe Hickey financed a stand-alone floor for his product at the new White’s Chapel Street store, which ironically was leased from Arthur M. Rosenberg. Izzy White’s bet forced competitors to divert cash from custom tailoring to readymade inventory on the floor, a trend interrupted by the onset of World War II.

Lester Isenberg enjoyed a robust custom business wedged between the Yale Architecture School and The Yale Dramat. He was a war hero decorated with many medals, and returned to York Street to find the custom business kaput. Isenberg’s was reinvented as Gentree’s and was decorated to the nines like an English pub. When the business closed in the ’70s, it was indeed converted from a clothing store to a pub.

Sam Rosenthal, a debonair Maurice Chavalier double, and Moe Maretz, a no-nonsense technician of the tailoring arts, exited Rosenberg’s and translated their savoir-faire into a faux Savile Row showroom on Fifty Second Street. They expanded their customer base with luminaries from the entertainment world that included George S. Kaufman and his coplaywright Moss Hart. The world premiere of “My Fair Lady” took place on February 12, 1956 at the Shubert Theatre in New Haven. Hart directed the landmark musical and steered costumer Cecil Beaton to Rosenthal-Maretz, who tailored Rex Harrison’s classic Henry Higgins wardrobe in their New Haven workrooms.

Many of the Ivy League clothiers were former J. Press employees. The exodus began in Cambridge in the late ’30s. Mort Sill and Jonas Arnold left Press and opened up Chipp on Harvard Square. Sill left shortly thereafter to start an exclusive New York custom tailor enclave. A complicated journey ensued as Chipp opened briefly in New Haven before reopening in 1947 in New York upstairs from The Gamecock, a trendy 44th Street bar.

Arnold soon joined his new partners, Lou Prager and Sidney Winston. Prager had managed the Press store in Princeton that closed during World War II, and Winston represented Press at Williams, Dartmouth and many Northeastern boarding schools. Chipp mirrored Press and Feinstein, but brought more flair and color to the table. It served an honor roll of customers from Cafe Society, the corporate power elite, and top echelons of government, eventually outfitting President Kennedy and much of his retinue in The White House.

Continuing the merry-go-round, Chipp roadman Ken Frank, along with Mike Fers and talented fitter Pete D’Annunzio, started Lord of New York, next door to Chipp and upstairs from J. Press. Lord had some success for a decade siphoning off an edge of the establishment crowd.

Running full circle, Mack Dermer and Sam Kroop, Midwestern and West Coast J. Press roadmen, took over Arthur M. Rosenberg and gave it a good run in Langrock’s original New Haven premises.

Brooks Brothers, never willing to surrender its role as the first-rank purveryor of the Ivy League Look, maintained a surreptitious presence in New Haven with biweekly showings at the Hotel Taft.

The Yale Coop (before the surrender of its clothing premises to Barnes & Noble) offered discounts to its student members and sold mid-price goods that ran the gamut of standard Ivy garb.

Moving on, De Pinna of New York sold hand-tailored Oxxford Suits, Douglas MacDaid featured the nationally popular Rogers Peet line on Chapel Street, and Jay Rossbach, who married into the Saks Fifth Avenue Gimbel family, originated a Saks University Shop between Morey’s and Whitlock’s Book Store.

And the Ivy heyday in New Haven was not limited to the retail sector. Thousands of oxford-cloth buttondown shirts were made every day at the Gant, Sero and Tanger factories in the industrial neighborhoods off State Street.

This is not a history thesis, but a personal memoir. The Golden Oldies of the heyday are gone with the wind, yet J. Press still keeps its doors open for business at 262 York Street, the last surviving remnant of an iconic past. — 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.

Images via Sorrentolens, AldenPyle and The Ivy League Look.