Welcome to The Ivy League Look

This blog presents a historical view through articles, photographs, reminiscences, and advertisements, of an American style of men's fashion of the mid-20th century known as "The Ivy League Look" or "The Ivy Look."

This blog will not present modern-day iterations of this "look"; it will be shown in its original context as an American style worn during this specific era. Author commentary will be kept to a minimum.

This is not a commercial site and links to commercial sites will not be posted.

April 21, 2009

Chipp - Walk Before You Run - 14 East 44th Street

"Chipp opened its doors on April 1, 1945. (My brother insists it was 1947; when I get a few free moments I will research it.) The Brooks Brothers flagship was, and still is, at the corner of 44th and Madison. J Press was on the second floor on the northeast corner of 44th and Madison. The Yale and Harvard clubs were within shouting distance. The Biltmore Hotel, with its famous “Meet me under the clock at the Biltmore”, was around the corner. This was the place to be.

In those days, we rented just the second floor in the brownstone at 14 East 44th Street. A famous watering hole called The Gamecock, which occupied the ground floor, was frequented by the advertising fraternity. (These were the “men in the gray flannel suits.”) Our customer base was primarily the men who Sidney Winston, my father, met when he had traveled the Eastern prep schools for J Press: young boys who had now matured into business leaders, and, in some cases, world leaders. He was the same age as his young prep school customers. As a result, the relationships that developed were very different from relationships that are made when one is older. Many of those customers remained loyal Chipp customers through their entire lives.

The bill of fare was custom clothing and special-order clothing. (Stock clothing on the rack would not be part of Chipp for a few years.) And the key was being where the action was: the infant Chipp’s famous neighbors drew many potential customers onto the street. My father and his partner at the time, Lou Prager, who also earned his spurs at J Press, would go down the narrow flight of stairs to 44th Street and snag the men they recognized. There was no elevator—many famous people trudged up that flight of stairs.

As the business grew, the third and then the fourth floor were rented. In the mid 1960’s (I think it was 1965), we bought the entire building, opening the ground floor storefront. The fifth floor became a true retail specialty operation.

In about 1985, when a lot of New York City properties were being bought by Japanese interests, we sold our building. After a brief incarnation on the second floor of 342 Madison Avenue (we occupied the space at the corner of 43rd Street), we moved to our present address, 11 East 44th Street, right across the street from where we began.

We have come full circle. Again we do custom and made-to-measure (special order) clothing. No clothing on the rack. I am sure my father on high is amused."

- Paul Winston


Chipp 2 / Winston Tailors Blog

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