When Mad Men Ruled The Roost

The party’s over. Madison Avenue sidewalks, bare of shoppers, remain a ghostlike remnant of the celebrated Mad Men era when teeming shoppers and classy shops were stuffed like salamis north of 44th Street. Americana period drama television series Mad Men ran a fabled take of the era on cable network AMC from 2007-2015. 

“Mad Men” was a slang term referring to 1950s admen working on Madison Avenue used to refer to themselves, “Mad” being short for Madison Avenue.

The series protagonist, Don Draper (Jon Hamm) was a womanizing, hard-drinking, chain-smoking emblematic of the times. He and his bros arrogantly marched up and down Madison Ave. flaunting their grey suits tailored in a variety of shoulder styles from three button natural to two-button square. Adjacent shops in the quadrant of 44th Street to 57th served them well. 

A classic romantic-comedy-drama, Billy Wilder’s 1960 film The Apartment, further epitomized the epoch starring occasional J. Press customer (since his Harvard days) Jack Lemmon. Drawing a bead climbing the executive ladder, 1960s corporate amorality ruled the roost with scenarios chronicling pre-Harvey Weinstein Me-Too aggressions. 

Caravans of Mad Men admen boozers hoisted three hour-three Martini lunches at The Gamecock on 44th Street between 5th and Madison. The 1961 J. Squeeze New York store above the fray was squeezed in a tooth paste tube premise at the northwest corner of Madison and 44th Street. 

The offbeat location around the corner from the legendary preppy gathering place, Clock At The Biltmore, at school vacation and cash-sale times provided a line of wannabes from the Squeeze elevator all the way out the door to the sidewalk. The narrow space was coming apart at the seams when Harry Macklowe, a pushy lease dealer prior to becoming incendiary real estate mogul, strutted off the elevator. “I’m gonna make a deal,” he told Irving Press, “to move you downstairs to the other side of Madison into the space currently occupied by the Atlantic Coast Railroad.”

Harry got us out of our lease at the right time in booming 1962 Camelot. The first-floor selling space was 3,200 square feet with Ivy Style window displays on the street utilizing their full six-foot depth Irving copied the window format of his New Haven-York Street headquarters. During frequent travels to England he drew inspiration from window displays he studied in London’s Burlington Arcade.

The new quarters were also next door to The Gamecock. Irving Press savored his chops upstaging competitor Chipp owned by former J. Press employees occupying second floor quarters upstairs from the booming saloon below and no sidewalk window displays to highlight their “go-to-hell” otherwise famous pants.

Brooks Brothers held forth its leadership role in its multi-storied 1912 landmark building at 346 Madison with Paul Stuart a block away harboring a mid-block location on 45th Street. Paul Stuart’s clothing was manufactured by Grieco Brothers-Southwick utilizing the same make as its mid-priced neighbor, 6th Floor Brooks Brothers labeling Stuart, “Poor Man’s Brooks Brothers.” New Haven tailor Arthur M. Rosenberg burrowed across the street next door to romantic Abercrombie and Fitch, highlighting their unlikely combination of hunting and safari gear together with soft-shoulder three-button Ivy. Moving uptown, F.R. Tripler at 46th and Madison pushed a quantity of goods manufactured in upstate Rochester by its former owner Hickey Freeman featuring square shouldered corporate pseudo formal wardrobes. Rex Harrison’s My Fair Lady New Haven custom tailor Rosenthal-Maretz faced office staff popular Hamburger Heaven on 54th Street. J. Press New Haven neighbor Fenn-Feinstein was situated west of Madison on 57th Street. This retail ambiance occurred at the time salesman Ralph Lauren was pushing cravats behind the tie counters at Brook Brothers and with Fred Pressman dynamically marketing off- price quality goods in his Barney’s family emporium on 17th Street.

I may have left out or forgot some key players, but octogenarian memory only goes so far. Don Draper and his guys poured cash into all the nearby clothing parlors enabling Mad Men sartorial armor. Draper offers the final take,

Nostalgia—it’s delicate but potent…Teddy told me in Greek nostalgia literally means ‘the pain from an old wound.’

It’s a twinge in your heart far more powerful

than memory alone.



J. Press Mad Ave


1 comment

Mr Press,
Just read the demise of Brooks Brothers in WSJ,glad to see Press stays as the last curator of The Ivey Look.Long live J Press
Vincent McKelvey
Weatogue Ct

Vincent McKelvey July 09, 2020

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