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.

Showing posts with label Chipp. Show all posts
Showing posts with label Chipp. Show all posts

August 2, 2011

June 3, 2011

An Offer Worth Considering, Chipp

The following offer is good for the next three days ONLY:

Purchase one bespoke suit tailored using Holland & Sherry’s Escorial* fabric for $625,000 and I will give you, absolulely for free, my town house condominium located on Preakness Mountain in Wayne, NJ and a black Saab SUV, which is in perfect running condition and has less than 18,000 miles of use. The town house will be unfurnished. The Saab will have a full tank of gas.

Chipp 2 Blog

Escorial® is a fibre rich in history and geography. Travelling the globe from North Africa's highest mountains, to the El Escorial palace in Spain before reaching Australia and New Zealand centuries later. The Delicate, time consuming processes, from harvesting the fleece to the finished fabric, as well as its unique heritage, makes Escorial® the most exceptional and purest fibre in the world. In mankind's constant quest to discover the finest. Escorial® is the fulfilment of that dream. Nothing comes closer. Today Escorial® is the world's finest naturally grown fibre, so rare there are only three remaining flocks in the world purely descendent from the original royal Escorial flock. One in New Zealand and two in Australia, where breeders are still committed to preserving the legacy of these fine merino sheep. Then only through a limited selection of the best spinners and weavers does Escorial® find its way into the finest of clothes.

May 12, 2011

Madison Avenue Sets the Style, 1956

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"The clothing style now favored by the men of Madison av. is what is loosely referred to as Ivy. This trend is significant because Ivy has long been associated with the avenue. A group of tradition minded men's shops on Madison - on which Brooks Brothers is the most noted - have carefully nurtured, preserved and defended the style for more than 60 years."


Apparel Arts/Esquire - 1956

May 3, 2011

Customized Seercord Suits, 1950

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1. Natural Shoulders
2. No front dart
3. Raised lap seams
4. 10 inch hook vent
5. Regular pockets and flaps
6. Ocean pearl buttons
7. Tapered trousers without pleats


The Daily Princetonian - 4/14/1950

April 25, 2011

May 31, 2010

"Chipp Has the Stuff", 1948

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The Cavalier Daily (University of Virginia) - 10/16/48

April 22, 2010

Allen Solly at Brooks Brothers, 1963

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Pittsburgh Post-Gazette - 5/22/63

Also see the Chipp 2 blog by Paul Winston for more information on these shirts.

April 6, 2010

Ivy and Oddities, 1962

Princeton's Ivy Club

Newest red fashions

...more red

...and knickers


LIFE magazine - 9/21/62

March 5, 2010

Fat Max and Slim Jim, 1966

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"(Brooks Brothers) has kept the width limit at three inches on its exclusive first floor, while letting it reach four in its university and young executives' department.

J. Press and Chipp, two of Brooks Brothers' competitors in the city's tailoring enclave off Madison Avenue at 43rd Street, also sell the wide ties, like Brooks in sober regimental stripes and club patterns."


Associated Press, July 1966

[Ed. note: See also this J. Press advertisement (look closely at the bottom of the ad)]

November 27, 2009

October 6, 2009

Bespeaking of Suits, Chipp

Bespeaking of Suits

Trading up to Custom

by Linda Dyett


Co-existing in the low-Forties ambit of the Yale, Princeton, and Harvard clubs is the other upmarket trio, Brooks Brothers, J. Press, and Chipp of New York -- all specialists in the button-down shirts and the sack suit. Brooks Brothers dropped its custom-suit department in 1976 (though, by special order, it still does made-to-measure). Press does a fair job with both custom and made-to-measure. As for Chipp, "no one," says G. Bruce Boyer, "surpasses them in making suits in the classic American tradition."

Chipp is one of the most pleasurable American-oriented men's stores around. Cyrus Vance buys his suits here. So do Jamie Wyeth and a major New York fashion designer-sophisticate whose name I can't reveal because one of his sub-licensees is a men's-suit line.

The far end of the well-planned new interior is a quiet, librarylike setting where the custom and made-to-measure wares are sold. Its shelves are filled with gorgeous Scottish Cheviots, handwoven Shetlands, estimable flannels and tweeds, and a stunning collection of Lesser & Sons woolens. Sipping, perhaps, at a glass of Jameson scotch [sic] from the discreet cherrywood-paneled bar, you're bound to wonder what better ambience there could be for choosing a business suit.

And then there are the owners, the Winston brothers, with their funny, off-beat personalities. They're brilliant at making clothes-shopping endurable for men who hate to shop. Imagine equal measures of Woody and Steve Allen trying to sell you a suit.

If you go the made-to-measure route, you'll get a traditional style priced at $500 to $900, plus and extra $40 for cut-through sleeve buttonholes, and the finished product will be ready in six to eight weeks. The custom-made suits start at $1,100, vests at $205. At least some of the excellent craftmanship is provided by an outside contractor, but Chipp's old bushelman is right on the premises to do the fine detail work. So valued is this man, says Jim Winston, that he's kept "absolutely out of sight, with a towel over his head."

You can order almost any custom style your heart desires. André Leon Talley, a House & Garden creative director, recently had Chipp do a snug-fitting hunting-jacket suit with a high-rolled lapel, deeply slanting pockets, and cuffed sleeves meant to be turned up to reveal a flame=red printed-silk lining - a gift to Talley from Tina Chow. The trousers have single reverse pleats and an extension waistband. The style, in covert cloth and carefully modeled on one worn by Jack Bouvier, is proof positive that Chipp can accommodate even very outré wishes. The only taboo here is the heavy-shouldered, oversize look.

The house specialty is unusual jacket-lining fabric, including Liberty, foulard, and challis prints. Or you can have solid-colored Bemberg, and lighter-striped rayon for the sleeves. The Winstons know all about traditional tailoring.

Chipp of New York, 342 Madison Avenue, at 43rd Street, second floor; 687-0850. Open Monday through Saturday from 9 a.m. to 5:45 p.m.


Excerpted from New York Magazine - 2/15/88

October 5, 2009

Cyrus Vance, 1967

US envoy Cyrus R. Vance meeting with Pres. of Cyprus Archbishop Makarios.


Google's LIFE photo archive

September 1, 2009

The Ivy Look Heads Across US, LIFE, 1954

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Top: HOUSTON INSURANCE BROKER Alex Dearborn, Sewanee '50 wears classic three-button suit bought from representative of New York's Chipp.

Bottom: ATLANTA AIRLINE EXECUTIVE William Magill, University of Chattanooga '38, wears "natural look" gray suit from Rich's department store.

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Natural-shouldered suit becomes a new male uniform

The "Ivy League look" identified with determinedly inconspicuous New England males for over 50 years and with Madison Avenue advertising men for the past 10, has now got out of eastern hands and is making its way across the country (left and below). It has also got away from upper-bracket tailors and into the hands of cut-rate clothiers like S. Klein, whose advertisement (right) gives as complete and compact a definition of the look as has ever been written. The popularity of the natural-looking suit has widened quickly in the last two years as men became dissatisfied with pale bulky suits and flashy ties left over from their postwar splurge. Although the authentic Madison Avenue uniform perpetuated by Brooks Brothers and campus-originated shoppes like J. Press (p. 70) has nonexistent shoulders and fits so snugly that it looks a size too small, facsimiles from volume clothing manufacturers and tailors are less severe in cut. To reaffirm their individualism beleaguered Ivy Leaguers are considering adding a fourth button to their jackets or resorting to a radical new silhouette (p. 72).


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A New Haven institution which rivals Yale in some well-tailored hearts is J. Press, established in 1902 and now carried on by the founder's two sons. Its slope-shouldered product, which the Press boys consider the only acceptable dress for a normal Yale man, has scarcely changed over the years. Press has branch stores in New York and in Cambridge and maintains traveling representatives to replenish the wardrobes of scattered alumni customers. 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.

Top caption: PRESS FAMILY PORTRAIT in New Haven shows uniformly dressed salesmen standing behind founder's sons Irving, Yale '26 (left), and Paul.

[Back, left to right: George Feen, Sam Kroop, Gabe Giaquinto, Herman Racow. Front: Irving Press, Paul Press]

Right caption: YALE TACKLE Philip Tarasovic tries to minimize heroic shoulders.

Bottom caption: ODD JACKET, a style supposedly begun by a Yale student in 1928, is fitted to James M. Brown III (see p. 2 of linked document), Yale '56, in the same tweed worn by Press salesman.

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DRASTIC ALTERNATIVE TO IVY the "moderate Edwardian" silhouette now available only from custom tailors, appears in tweed suit worn by New York publicist Patrick O'Higgins. Made by Bernard Weatherill, it combines features of British riding clothes and a guardsman's uniform. Jacket flares in back and is four inches longer than usual. Pockets are at a deep slant and buttons on sleeve actually unfasten. Tapered pants are 15-1/2 inches at cuff.


LIFE magazine - 11/22/54

July 10, 2009

And Now for Something Completely Different*, Chipp, 1956

Silk is the perfect suiting for summer, but for men it has always had one big drawback. It has never had the adaptability of woolens and worsteds on the designer's drawing board and the weaver loom. Fine glen plaids have never been successfully incorporated into silk for the men's suits - until now. Gentry's stylists, working hand in hand with the master silk technicians of the Japanese firm of Kanebo, have finally licked the problem. Under this tissue you see a swatch of the first bolt of silk ever made with a glen weave. Superbly different in design, the material has still other remarkable qualities. It is a 4 1/2 ounce cloth, which makes for great lightness and coolness. It has fine wearing qualities, with a life span that will stretch through many hot seasons. Its wrinkles expired overnight on the hanger. On the facing page (above) you see the first jacket ever made of this cloth. We had it designed and executed by Chipp, custom tailors of New York East 44th Street, under the supervision of Robert DiFalco. It's a three-button model, buttonable at the top or middle. Its lapels are extra narrow. Its patch pockets are smaller than usual, in deference to the fabric's design. Its coin pocket is not patch, to stop your loose change from bulging. (The flap on this pocket can be worn inside or out). The jacket is lined with silk black pongee, full-lined to make it hang with perfect aplomb, and it has a long back vent. We consider it a handsome addition to nay man's summer closet; if you concur, you can take this blueprint to your tailor.


Gentry Magazine, No. 19, Summer 1956 from Gypsy Wear Vintage

*as in..."Tailored by Chipp, but it's not exactly Ivy, is it?"

June 11, 2009

Chipp, 1952

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The Chipp Ready-Cut is designed with soft natural fronts, shoulders without padding and small lapels...all important details of the conservative styling for which we are well-known.


Gentry Magazine - #5, Holiday Issue 1952, courtesy of DixieRising on The Curriculum

May 15, 2009

Circling the Square, 1940

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Tweedy Trio

"Chipp, Press and Ross, Cambridge custom clothing's big three, have a unique business technique. The three-button-natural-shoulder-loose-fitting long coats which they produce are, in their eyes, works of art, and they should be sold as such. The ordinary good tailor won't sell a suit unless it fits well; he's a piker compared with the Mount A. Street trio. They won't sell a suit unless it fits the personality of the buyer. Every piece of clothing that goes out of the little brick shops is designed to fill a definite function in the wordrobe of its owner."

Read the entire article here:

The Harvard Crimson - 11/20/40

Image source:

Bulldog: J. Press 1940 and 1941

Note: You might notice that the ad shown above is taken from the Yale Daily News. Same year, different Press location, but more than likely the same copy.

April 29, 2009

The Yale Man

The Yale man dressed impeccably in the preppy uniform of the day, though ''preppy'' wasn't in wide use then. ''Natural shoulder'' was what men's magazines called the Yale look, and for decades the clothing stores near campus at Elm and York Streets in New Haven were the natural-shoulder capital of the universe. Its bulwarks were Fenn-Feinstein and J. Press. In New York, not far from the Yale Club, there was Haberdasher's Row, commencing at 44th Street and Madison Avenue: Brooks Brothers, known as just ''the Brothers''; J. Press (there was also one in Cambridge, Mass.); and Chipp, which had a retail store but also did big business in custom tailoring. (We have Chipp to thank for, among other innovations, jackets and trousers of patchwork madras.)

In the 1950's and 60's, an experienced observer could tell where a Yale man shopped just by his shirt: plain pocket meant Fenn-Feinstein; pocket with flap, J. Press; and no pocket at all, the Brothers, which in those days didn't believe in shirt pockets, perhaps because almost all their suits still came with vests. Vest aside, to determine the origin of a suit might take closer observation; if it had a lining of bright red silk (like several of the suits of one of my classmates, a guy so Cole Porter-ish that, like Porter, he kept a piano in his room), it was most likely a custom job from Chipp; if it had a button fly, it was probably from the Brothers, which still sold such garments up on the geezers' floor, where you could also get voluminous high-waisted boxers of the kind sometimes on display in the Yale Club locker room. They had three buttons at the top and came up almost to the nipples, as if made with a built-in cummerbund.

All the sartorial niceties of the Yale style began to erode, as I've suggested, with the enrollment of what became the class of 1968 -- my class, as it happens, and also the class of George W. Bush. I seem to recall the president-to-be going sockless and wearing corduroys and cable-knit sweaters, but that could describe any number of us. He did not cut the figure of, say, Strobe Talbott, another classmate, who became deputy secretary of state during the Clinton administration. Strobe was a full-fledged intellectual, so he could carry off the affectation of wearing plaid Bermudas well into November.

Article source:

The Yale Man - NYT - 9/19/04

Photo source:

A Restless Transplant - Brian Kupke and his Yale Sweater


Old School (Thanks!)

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