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

How cool was it to dress Ivy during the heyday? Cool enough for the El Capris, an African American doo-wop band from Pittsburgh, to cut a B-side called “Ivy League Clean” in 1958.

The song failed to chart, however, and the band became just another forgotten doo-wop band whose name starts with “El.”

That is until the days of YouTube and blogs. So let’s raise a glass (strawberry milkshake seems appropriate) and toast those long-gone days when pop artists would actually sing about wearing a buttondown collar, striped tie and Tyrolean hat. My favorite line is:

When I come to the gig
I’m sharp as a tack
With the tassels on the shoes
And a belt in the back

And make no mistake: Those who fail to dress clean-cut will be swiftly punished:

If you wear big shoes
And a wide open shirt
When you come around
You’re sure to get hurt

The funny part is that a hipster band singing the same lyrics today might actually be kinda cool.

What goes around comes around. One of the great laws of physics. — CHRISTIAN CHENSVOLD

For Ivy Style’s 300th post, London-based contributor Rebecca C. Tuite examines the most important piece of literature about The Ivy League Look’s most important brand.

There is little doubt that Mary Mccarthy’s short story “The Man in the Brooks Brothers Shirt” is now probably more famous for its punchy title — a dream for the Brooks Brother’s marketing team —  than it is for the actual story. But it remains a classic part of the mystique of the Brooks Brothers Look, and indeed, the Brooks Brothers Man.

Taken from Mary McCarthy’s 1942 novel “The Company She Keeps,” which is less a straight narrative and more a collection of six short stories, “The Man in the Brooks Brothers Shirt,” forms the third chapter in the story of Margaret Sargent, a young woman trying to redefine her life following a Reno divorce. “Floundering in a world of casual affairs and squalid intimacies,” Sargent is self-destructive, reinventing herself as a bohemian and rebelling against society, all of which finds a perfect counterpoint in Mr. Breen: a Cleveland-based executive at a steel company and the “hearty stranger in the green shirt” she meets on a Pullman car heading west to Sacramento.

The story opens with the first description of the man, who at this point remains nameless:

The new man who came into the club car was coatless. He was dressed in grey trousers and a green shirt of expensive material that had what seemed to be the figure “2″ embroidered in darker green on the sleeve. His tie matched the green of the monogram, and his face, which emerged rather sharply from this tasteful symphony in cool colours, was bluish pink.

Less than impressed, Sargent sees him “like something in a seed catalogue,” and although feeling “full of contempt for the man, for his coatlessness, for his colour scheme, for his susceptibility, for his presumption,” she still allows herself, firstly, to enter into conversation with him, and secondly, to spend the night with him (subsequently enduring the following morning). All of this is peppered with Sargent’s own disgust for the promiscuity her aunt has always warned her about — “I don’t know why you make yourself so cheap,” and “It doesn’t pay to let men think you’re easy.” (Continue)

As a follow-up to our previous post on the Brooks Brothers women’s collection moving back into the Madison Avenue flagship, we take a look at a 1954 LIFE Magazine article and newly discovered LIFE archive photos depicting the trend of women buying boys and mens clothing at Brooks. The photos also reveal what the store looked like in 1954, when clothing was predominantly laid flat on tables.

Although Brooks Brothers didn’t officially launch a full women’s department in its flagship store until 1976, young American women had been infiltrating the bastion of sartorial masculinity for quite some time. Since launching its pink shirt for women in 1949, Brooks had begrudgingly acknowledged the large number of females who wanted to wear the brand.

But within five years women were no longer satisfied with a tiny customer service desk located in a dark and secluded area of the store: They expected to roam freely through the store at will — including, presumably, the changing rooms. This growing inclination was reported in 1954 by LIFE Magazine, which suggested it was a case of Brooks giving an inch and girls taking a mile, like roaming the store in dressing gowns. (Continue)

With this post Ivy-Style bring Preppy Week to a close. Click here to have the Dead Kennedys’ “Terminal Preppie” play in another browser window as you rejoice in the demise of Biff and Muffy.

Every trend carries within it the seed of its own negation. The hype and expectation over “Take Ivy” has made it fashionable to take a blasé attitude towards the book, complaining online how the photos aren’t in HD. The middle road, as usual, is the best: The tome is neither the Rosetta Stone of Ivydom, but nor does it warrant flippant dismissal. Likewise, perhaps the current Preppy-Ivy-Trad-Americana trend will give birth to a hippie revival in a few years, the very trend that followed the original heyday of the Ivy League Look.

In the early ’80s, the immense success of “The Official Preppy Handbook” saw an immediate backlash by would-be humorists looking to cash-in by lampooning the new popped-collar zeitgeist. Kate Reed’s “101 Uses for a Dead Preppie” came out in 1981, followed by “The Joy of Stuffed Preppies” by Randall C. Douglas III and Eric Fowler the next year.

If you want copies, better act fast. I picked mine up for a few bucks each several months ago — about the same price I paid a few years ago for the Preppy Handbook, which is now commanding a premium on eBay. (Continue)

Preppy Week continues with this impressive bit of research from Greg Moniz, a student at Connecticut’s Trinity College, who brings back our “Somewhere in Time” series by compiling highlights from Time Magazine’s coverage of the ’80s preppy trend.

“If one more person comes in here and asks for Bass Weejuns, I think I’ll scream,” says an Atlanta saleswoman in a 1980 article from Time Magazine. A more muted but equally frustrated voice can be heard from a Time writer in an article several months later while writing about New York’s soon-to-be-closed Biltmore Hotel: “Years before alligator shirts covered every second American torso, long before artifacts of Ivy League style were mass-merchandised, before anyone dreamed of writing an ‘official handbook’, Manhattan’s Biltmore Hotel was the premier place for preppies.”

The writer goes on to paint a dazzling scene: “Within its vaulting rococo spaces, numberless Princeton boys leered at an endless parade of Vassar girls, while Dartmouth seniors, a little tight, chatted up Smithies. The bubbliness was swell and incessant.”

Both the saleswoman and the writer express a certain anger, but for different reasons. The saleswoman can’t keep buyers from flooding the gates in search of “Oxford-cloth shirts and Shetland sweaters, khaki slacks and tartan skirts.” (After all, the reason she’s interviewed is because of a burgeoning preppy America.) But the writer sees the demise of a stale, previously grand hotel as representative of the state of prepdom in the 1980s. With the Biltmore gone, what do preppies have left to define themselves? Certainly not the clothes on their back, as every Brad and Tiffany now have the same.

How is it that one single media outlet was painting two vastly different portraits of prepdom? Because just as it was making its grand appearance on the national stage, with its lifestyle glorified, replicated, exaggerated and mocked, classic prepdom was also on its deathbed — its subtle, idiosyncratic, authentic self mourned by its faithful, destiny-driven band of originals.

A review of Time articles from the 1980s reveals the two parallel storylines, with death and a culturally dominant, more egalitarian rebirth as two prevalent themes.

So here’s the best of Time‘s coverage and commentary as the old preppy order was dying off and a new one was being born. I’ve provided some of the more colorful excerpts; you can click the links to read the complete articles for free at Time.com. (Continue)