Contributing writer Christopher Sharp takes us on an epic journey through the 20th century, charting how madras went from obscure resort wear to a national craze during the “guaranteed-to-bleed” days of the Ivy heyday.

If I were to create an Ivy-inspired urban myth, I would spin a tale of how the first Yale man to wear a madras shirt was old Elihu himself and how madras money built Yale.

“While no one knows why preppies are so attracted to madras,” Esquire once wrote, “it is a matter of record that Elihu Yale was once Governor in Madras and included five bolts of the fabric in his initial endowment to the University.” This story was first told in a 1960 Hathaway shirt advertisement and was the product of David Oligivy and his minions of Mad Men. An overly investigative personality might wonder if these five bolts are the ones described as “five pieces of plain muslin” in the History of Yale provided by The Society of Colonial Wars in the State of Connecticut.

Journeying back to the turn of the century, madras in plain and striped varieties was known to the American customer. The 1897 Sears Roebuck & Company catalog list madras shirts for sale, and the New York Times in November 1919 reported a madras shirt shortage.

Esquire reports that madras first appears in the fashion pages in 1937, noting swim trunks being seen in South Hampton, Long Island, and Newport, Rhode Island. Madras was definitely known to the New Haven haberdashers of the time, who sold it as resort wear. One example is madras swim trunks sold at J. Press in 1939. It has been widely believed that Americans visiting the British West Indies at the time brought back this look.

As a resort wear phenomenon, some of the credit can be given to the Bermuda Athletic Association, which invited Ivy League rugby teams to a tournament in 1935. The pilgrimage became so popular that charter flights for students would be booked and advertised in the student newspapers. The students returned to campus with new wardrobe items and a taste for island revelry. LIFE Magazine predicted in 1948 that the students accustomed to coming down over break would return again for their honeymoons.

Instrumental in the spread of resort wear were the island outfitters: stores like Trimingham’s, Smith’s and the English Sports Shop. These places were the source for proper Bermudas, Shetland sweaters and everything madras. The resort trend fueled an interest in madras through the postwar 1940s. A glimpse at the future 1950s madras scene appeared in the December 5, 1949 issue of LIFE Magazine. In that issue they feature Robert Smith in East Hampton wearing a plaid madras shirt, and a bare-chested, pipesmoking Pierre S. du Pont III sporting a pair of plaid madras swim trunks on Fisher Island.

Madras would continue to make its rise in the 1950s. The fledgling Gentry magazine would feature madras swim trunks in 1952. The summer 1953 issue features the madras blazer.  The editors write “Cotton madras from India, the multicolor plaid-patterned fabric with a faded look, popular in sports shirts and swim trunks, now makes its appearance in another hot-weather item. It was introduced and immediately accepted in Palm Beach this winter.” The photos and accompanying text feature Ivy League jackets, three-button and “worn without shoulder pads.” LIFE Magazine also featured a couple wearing madras in 1955, and Sports illustrated would feature madras in 1956, 1958 and 1960.

Robert Ruark, sportsman and author of the evocative Southern work “The Old Man and the Boy,” wrote in his syndicated column in 1960, “My madras shirts and shorts are guaranteed to ‘bleed,’ another Madison Avenue dramatization of simple color instability, such as may be found in any ordinary shirt with no press agent.” Ruark may have been sanguine in regard to his bleeding madras, but the American market on the whole had to be sold on it.

Ellerton Jeette, president of Hathaway shirts, had been anonymously making white madras shirts for years.  It was on a visit to London he noticed a bespoke shirtmaker cutting shirts out of plaid madras. This tartan-inspired fabric is believed to have its roots in the 19th-century Raj in India, when local weavers incorporated colonial patterns.

There was only one problem with the shirts when first introduced: They were rejected by the American public. Customers claimed that they bled and faded in the sun. Returns mounted and disaster loomed, so Jeette took his problem to master advertising man David Ogilvy.

It was in 1951 that Ogilvy brought the sleepy New England shirt company to national attention by introducing an eye-patched icon dubbed “The man in the Hathaway shirt.” Jeette was looking for another stroke of advertising genius, and told Ogilvy that the vegetable dyes in madras naturally faded. “Then why not say so?” replied Ogilvy.

At that moment madras’ chief flaw became it most prized virtue. Over the years the Madison Avenue spin machine churned out promises like “Hathaway guarantees that your shirts will fade in the wash,” and “Magical things happen to this shirt when you wash it.” Upping the ante, bleeding and fading were said to provide “good breeding and maturity,” something unseen in mass-produced fabric. Madras left to its natural course would produce a shirt “marvelously muted” and “dustily well-bred.”

“Unfaded madras garments are as rare as a pair of clean white bucks on a college campus,” reported The Evening Independent on July 26, 1960. In the same year an anonymous storekeeper reported, “So far as my customers are concerned, the sooner the madras fades the better they like it.” It seemed the Olgilvy strategy worked and the first half decade of the 1960s would see madras reach mass popularity.

In January 1960, the Wall Street Journal reported that the hottest thing in menswear was madras shirts and sports jackets. Esquire’s fashion director OE Schoeffler continued the drum beat in 1963, trumpeting madras as “bigger then ever.” He notes that madras was still being used for sports shirts, jackets, shorts and swimwear, but the new trend was for madras ties, belts, hats, watch bands, vests, wallets, tobacco pouches, cigarette cases and shaving kits. A UPI story from July 1965 reports that madras sales were strong in the summer of 1964, “carried through the winter in the form of pile-lined madras parkas and long sleeves sports shirts and picked up steam this summer.” The big sellers in the summer of ’65: walk shorts, sports shirts, three-button sportcoats and slacks. UPI also noted that patchwork jackets, which first appeared in Palm Beach a decade earlier, were “gaining ground.”

All good trends, however, must come to end. Madras would eventually use colorfast dyes — to the delight of Middle America mothers. America would go through a counterculture and see a rise in the popularity of workwear, and madras would retreat back to the college shops to be discovered again by the preppy crowd of the late ’70s.

The curmudgeons among us will say we have once again reached madras saturation. I look around today and the shorts seem too long, too loud, and they always seem to be paired with t-shirts. I get the feeling that the youths that wear madras today are the same sort that would be provoked to violence by the mere sight of it 30 years ago. At those moments I console myself with thoughts of a simpler time when you always wanted to have at least one friend who wore madras trousers because he always knew where the best parties were.

And when I need an extra bit of levity, I think of Early Shiply, retired clown and publicity man for Ringing Brothers, Barnum & Bailey Circus. When the circus came to New Haven in the spring of 1960, Shiply took one look at the students and quipped to the Yale Daily News, “If you see clowns one day wearing blue serge suits, it’s because you college kids are stealing our trademark with your madras outfits.” — CHRISTOPHER SHARP