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)

Preppy Week continues with this pre-OPH exploration of prepdom from the August 27, 1980 edition of The Toledo Blade.

Everything you always wanted to know about prep but were too stuck-up to ask
By Mike Steere
Blade Staff Writer

For lack of a better word, we’ll stick to the label that has been so cavalierly sewn on the recent resurgence of classic conservative clothing — Preppy.

What Preppy really means is someone who went to a fancy eastern boarding school, which is to say somebody whose daddy and grandaddy had pots of money.

In clothing, the word denotes a style based on a small number of expensive, natural-fabric, subdued-color pieces. The things that have been worn for at least 35 years by the spoiled scions of old money.

The basic idea of preppiness is to look rich and as though you’ve been rich so long you don’t have to flash it.

The hard part of it is that you have to look rich while wearing different combinations of a half-dozen garments that come in dull colors and crumple up as soon as you put them on.

There are rules here. You can’t, for instance, money up your appearance with Las Vegas displays of gemstones. Nothing gaudy is allowed.

Preppy is not an easy look. If you don’t FEEL preppy, you can’t possibly look preppy.

The idea is to wear a $250 blazer and $80 slacks like coveralls. Even if you got it last week, the prep ensemble should look as if you were born in it and that, at the time of your birth, your father was wearing the same thing.

Prep knows no age. The basic prep components are about the same from high school through retirement.

There’s nothing new here. For at least 35 years — through all the vagaries of fashion weather — the ship of classic conservatism has sailed on. The same people have bought traditional in the same places, and they will continue to do so until the last martini is mixed and the last bridge hand dealt.

If you want to wear these time-honored styles with authority, it is necessary to look like one of those people. With the newcomer to prepdom in mind, we have prepared the following short encyclopedia of prep.

The Preppy Look For Men

From Frank Kahle, owner of Neil’s Men’s Shop in Ottawa Hills, one of Toledo’s shrines to traditional clothing:

Like most people who are serious about this stuff, Mr. Kahle doesn’t like calling what he sells “preppy.” This appellation is merely a glib commercial label for a system of dress whose devotees are, like Mr. Kahle, religious.

This man is an absolute fetishist for tradition. If a garment isn’t cotton, wool, silk, or lambskin suede, he wants nothing to do with it.

To be a purist, he says, is to cultivate snobbery.

Basic prep items, according to Mr. Kahle, are the all-cotton button-down shirt, cotton khaki trousers, Shetland woolen sweater, serge regimental-striped belt, wool blazer, and the various species of Ivy League shoe.

The khakis are “the jeans of traditional clothing.” Mr. Kahle also acknowledges the admission of blue denim jeans and corduroy Levis to prepdom. Regretfully.

Ties ought to be silk, maybe wool or cotton for summer, in either a regimental stripe or Foulard pattern, (plain field with rows of little colored cells). The apogee of tie tradition is a burgundy and navy-blue regimental stripe. A true believer might have two or three of these.

Mr. Kahle frowns on club ties, the ones with little sporty things like pheasants, golf clubs, or sailboats.

A preppy pretender, Mr. Kahle says, can be spotted at 100 yards.

Suit or suit jacket shoulders tell the tale. Padded shoulders are very unprep, as are jackets with too much tailoring. True traditional clothing has natural shoulders and a sack shape.

Count the jacket buttons. Two is unprep. Three is the thing.

Pay attention to the rumple, Mr. Kahle says. Natural fabrics, unlike natural-synthetic blends, wrinkle. “Traditional clothing rumples, and it looks rumpled, and that is a very accepted, prestigious look.”

Pills around the collar – those minuscule fuzzballs – are another sign of the unprep, Mr. Kahle says. The pills only form on synthetic-blend shirts, which are not part of the purist’s wardrobe.

Cuffs are the stuff of tradition. You can get by with plain-bottom khakis, but Mr. Kahle encourages cuffs on all trousers.

The true believer doesn’t like new clothes. Certainly not new-looking clothes. The rapport between man and garment has to be relaxed and intimate, like old friends.

Your sheepskin suede sport jacket (ultra-suede is absolutely outré) doesn’t come into its own for two years.

Old preppy saying: “Weejuns aren’t worth a damn unless you’ve worn them in the shower.” Shoes should look broken-in. Shined, but never too shined.

Shoe advice from Mr. Kahle for women: Don’t move into colored Sperry Topsiders until you have a standard brown pair. Always build from the traditional ground up. (Continue)