Everything You Always Wanted To Know About Prep


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Everything you always wanted to know about prep but were too stuck-up to ask
By Mike Steere
The Toledo Blade
August 27, 1980

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.

The Look For Women

The garment vocabulary for women is more or less the same as the men’s prep pantheon – blazers, woolen pullover sweaters, oxford button-down shirts, penny loafers and slacks.

Also on the list, according to Madonna Corrigan, fashion director for Lasalle’s, are knee-highs or textured hose, kilts (plain or plaid), berets, plaid pants or bermudas, trench coats, and pea coats.

Jewelry is minimal. An acceptable piece, Mrs. Corrigan says, is the geometric pin.

The traditional dress code was established in men’s fashions, and most of the toniest prep women’s clothes come from companies that once belonged exclusively to men, Mrs. Corrigan said.

The Old Villager company, for instance, was a man’s shirtmaker that began making women’s shirts. One day it occurred to the owner to lengthen the woman’s shirt, and so the shirt dress was born. An original Villager shirt dress is fabulously preppy.

The rules of prep dress aren’t quite as rigid for women, Mrs. Corrigan says. There is room to play with colors and textures.

The traditionally dressed woman can, by making very small adjustments, transform her look from the school-girlish true preppy to a classic professional or dressy appearance. Penny loafers and argyle knee sox yield preppy, and textured hose and low pumps mature the appearance.

Good women’s traditional clothing is of the same weight and quality as corresponding men’s items. And the cost is about the same.

The trend toward high-priced taste is a sign of the economic times, Mrs. Corrigan says. The initial outlay for classics is high, but clothes of this caliber are investments that pay off over the years.

The Body

For men, broad-shouldered and athletic, but never overmuscled. Preps pushing 30 are sleek in a slightly dissipated way, the sort of body that is build on a regimen of martinis and light exercise.

Preps are never fat or overly robust. The prep body doesn’t call attention to itself. It is a rack for expensive clothes.

Prep women, like prep men, shouldn’t have overly generous proportions. This is a very good year to be flat-chested.

Preps should cultivate a sallow tan — outdoorsy, but not baked cocoa-brown. All things in moderation.

Parameters of the Preppy Life-Style

ANIMALS – Dogs can be very preppy. Tops are floppy, affable, big breeds that swim and retrieve. The Golden Labrador is as preppy as anything sold at Brooks. Any bird dog with a high-price pedigree is acceptable. It pays to spend a little extra for a distinctive breed. English setters, for instance, are preppier than Irish setters. Avoid miniatures and long-haired Orientals. If you must have a cat, a big tabby with a name like Bob, who has a few funny eccentricities, can dress up a prep household. No show cats.

WHAT TO FIND IN THE MAILBOX – Fraternity newsletter, alumni-association fund appeal, Bergdorf Goodman, Inc., fall catalog, and a letter from anyone on Nantucket.

WHEELS – Two seater convertibles. Sport car names with age — MG, Triumph, Austin, Fiat — are high on the prep list. The Japanese are building tremendous sports cars, but Datsuns and Mazdas somehow don’t achieve preppiness. It’s tradition, not how the thing runs, that counts. Classic Mercedes coupes, Jaguar XKEs, and restored Morgans are the absolute pinnacle. For family preppies, a green Volvo wagon.

SMOKES – Any American brand dating before World War II. The serious preppy smoker shuns filters. Smoke whatever dad smoked. English imports like Players are a very preppy option. Nothing funny-colored, too long, or menthol. For those who are quitting or cutting down (a very preppy thing these days), Benson and Hedges lights.

A PREPPY MEMENTO – Stateroom key from the R.M.S. Olympic (sister ship to the Titanic). Grandmamma’s 1927 crossing.

LABELS – Brooks (of course), Villager, J.G. Hook, L.L. Bean, Hickey-Freeman, Pendleton, Cole-Haan, Sperry, Etienne Aigner, Burberry, Izod, John Henry, Bass, Evan Picone, Calvin Klein, Sero, Troy Shirtmakers Guild, Southwick.

NUMBERS – For men, 3-1/2. In inches, it’s the correct width for jacket lapel, tie and shirt collar. The cuff on pants is 1-3/4 inches deep.

JOBS – Preppiest of all is an easy berth in Dad’s or Uncle’s company. Lawyer, accountant, or banker will do. It is very preppy to follow in male ancestor’s footsteps. Medicine can pass; if done in the correct, relaxed spirit. A preppy wants most of all to be able to wear fabulous suits to the office, take long lunch hours, and get away early for squash or skeet shooting.

POLITICS – GOP, as if you didn’t know. Distant involvement in politics, which to the true prep is a mite unsavory, like food wholesaling or auto parts.

FUN AND GAMES – Sailing, tennis, or any other racket sport, fly-fishing, volunteer work, tailgate parties at the alma mater’s football games, grouse hunting, and bridge. In all things the true preppy is a very sporting second-stringer — a better cruiser than racer. Marathon running, although very chic, is not preppy.

COLORS – For everything. Khaki, forest green, charcoal, maroon, navy-blue, white and camel.

LIBATIONS – The operative word is clean. Martinis, very dry. Scotch by the label. Bombay Gin. For mixers, tonic, soda, or water. Sipping sherry is acceptable, as is after-dinner liqueur, or brandy. Preppy soft drinks are apt to be gin drinks minus the gin – iced tonic or soda water with a lime wedge. Preppiest citrus is grapefruit juice. Booze is in decanters at home. For travel, silver flask with granddad’s initials.

FOOD – Fresh, never frozen. Meat cut to order. The prep-steak is New York strip 1-1/4 inches thick. Nothing from cans. Marketing is four-or-five stop adventure. Preppy moms bake secret-recipe oatmeal cookies for little prepsters. (Chocolate chips might make them break out).


HABITS – Regimentation — ordered and secure. No oversleeping. Social calendars. Little leather notebooks with lists of things to do. It is very preppy to slavishly follow any personal pattern observed in one’s family for three or more generations, whether or not it makes sense.

PREPOURRI – Helly-Hansen foul-weather gear. Wooden-shafted golf clubs. Watches worn inside of the wrist. Tortoiseshell glasses’ frames (See color photos of John Dean in Senate Watergate hearings). Gladstone bags. Anything British. Last year’s Topsiders repaired with sailing twine from dunnage bag on Uncle Roy’s ketch. Ancestor formerly on the board of Pierce-Arrow Motorcar Co.

Where Ivy League Traditions Began

The men’s Ivy League clothing traditions on which preppy fashions are based emanate from Brooks Brothers in New York.

This classic look might as well be known as the Brooks look. The venerable clothier, established in 1818, started and perpetuated the traditions of “traditional” clothing.

Brooks, according to a company spokesman, introduced the button-down collar about 1900, after one of the Brooks family had seen British polo players with collars buttoned down so they wouldn’t fly up during games.

At Brooks, the button-down is still called the polo collar.

In 1890, Brooks brought over from England the silk Foulard necktie.

The company introduced the Shetland woolen sweater for men in 1904, and they began selling the crew-necked woolen sweater for women in 1912.

The pink shirt for men — absolutely nothing is preppier — was born at Brooks Brothers in 1890. Women got pink Brooks shirts in 1949.

Seersucker and cotton cord are Brooks innovations from the 1930s.

Brooks gave birth in the United States to Argyle hose.

In 1918, the company made its first natural-fitting, three-button suit. Formerly, suit jackets had four buttons.

Brooks was also responsible for the first cotton-and-polyester blend shirt, an innovation which clothing purists won’t wear.

The coming-together of all the components of today’s preppiness didn’t transpire until just before World War II, the Brooks spokesman said. And the establishment of the “classic” collegiate look didn’t occur until after the disruption of campus life occasioned by World War II.

The Shoe

Guess — you’ll never get this one — how come the G.H. Bass and Co.’s classic penny loafer is called the Weejun?

It is not a cute contraction of an Indian name, an entirely plausible etymology for a hand-sewn moccasin made in Maine.

Weejun is short for Norwegian. The basic uniform shoe of prepdom is an import from Scandinavia.

According to Joseph Peach, Bass marketing director, Bass family members saw the shoe in Norwary in 1936, and bought permission to bring the design back home.

The distinctive yoke across the front of the shoe is for reinforcement, Mr. Peach said. He doesn’t know if the decorative slit was designed to hold coins, or how and when the first penny was put into the penny loafer.

The Weejun as we see it now is the way Bass began building it in the late 30s. Rolled leather on the sides and heavily decorative stitching are penny-loafer innovations introduced by other companies.

It wasn’t until the late ’50s that the penny loafer became a collegiate standard. One of the earliest indications that the Weejun was becoming a campus must-have was a 1960 note in the University of North Carolina Daily Tar Heel. Those “with-it” just had to have Weejuns, the Tar Heel said.

Prep-crazed 1980 Americans are buying Weejuns as fast as the company can make them.

Thanks to The Ivy League Look for originally finding this article.

20 Comments on "Everything You Always Wanted To Know About Prep"

  1. I like the historical aspects of this post.

    Again, the photo is great – same colors as the previous post – but I’m so into this particular look – i think its fantastic! Thanks again.

  2. This photo and the one below with red pants are both from an Ivy photo shoot in a Japanese magazine from 1982. I got the from Will’s blog A Suitable Wardrobe; not sure if they appeared somewhere else first (such as HTJ).

  3. Delighted to learn that my numerous burgundy-and-navy regimental stripe neckties qualify me as a True Believer.

  4. A second straight entry with a picture of red pants. Shoot me now, please. O plain khakis, where art thou?

  5. Where art thy plain khakis?


  6. thanks for braving a preppy week. nice find. the bit about tabby cats is so adorable.

  7. David V: Your response made my day. Proper use of “thy”, too!

    I went to great lengths to make sure my use of “thou”, a second-person singular noun, correlated properly with “khakis”. That’s a tough one to figure out, methinks.

    Also – please forgive my failed attempt at irony – I work at an office where EVERYONE wears the same color khakis, and almost everyday.

    I say if you’re gonna do red – do faded Nantucket Reds from Murray’s.

  8. Peter Carbonaro | September 9, 2010 at 12:17 pm |

    As much as I would fain* wear my faded Reds every day to work, I must sadly relegate them to Fridays and weekends. I, too, work at an office where everyone wears the same old khakis, everyday. Not that there’s anything wrong with that; it’s what they wear them with that’s the issue (chunky square-toe black sneaker/shoes, anyone?). Even the few times I’ve worn Reds to work, I’ve been given strange looks by the less enlightened. Nice to see there are kindred souls here.

    (* yes, I can use archaic English too.)

  9. Do you know where the picture was taken? It looks like the AD White Reading room in Uris Library at Cornell.

  10. Peter Carbonaro | September 13, 2010 at 6:55 am |

    Good eye. It is the A.D. White room. The wrought iron balcony gives it away.

  11. Great work but I take exception to “It’s tradition, not how the thing runs, that counts,” statement about cars and presumably everything there is. These things become tradition because of the quality, say how a car runs, not because of the name. Prep is about the thing, which is partly name sure. Items from so and so are dependable items from anywhere else are uncomfortably foreign. However, no prep wastes money and poorly running cars or shoddy items fall out of fav.


    It was originally a photo of me with a scotch rocks glass and cigarette in my right hand taken at Toledo Ohio, September,1980, wearing khaki trousers, starched white shirt and navy blazer.

    You’ve taken our text but done away with my photograph! Michael Steere and I were at school together, the University of Michigan at Ann Arbor. And in I believe Mike’s second year at The Blade, was asked to write a “Prep Guide”. He came to me accross the way and said, “Look here, you own more wool clothing than Australia could supply. How ’bout coming down to Toledo and we’ll bang this piece out together”.

    30+ years later, I still make notes, never oversleep, have possession to the RMS Olympic Stateroom key and will go to my grave defending the merits of a Pierce Arrow Motor Car, but, sadly, Uncle Roy no longer sails.

  13. Excellent read. Always thought Bombay was a fine gin – but more yuppie, no? Gordon’s is always choice.

  14. Charleston | May 13, 2012 at 1:16 pm |

    To DNM
    Ah, gin — there are a lot of fine choices these days. Beefeater 24, Plymouth, Boodles, and the ever-reliable Tanqueray and Bombay Dry. Gordon’s is better if one can get your hands on the green-bottled British-made Export (duty-free) or regular.

  15. I have to say I disagree with the statement “Count the jacket buttons. Two is unprep. Three is the thing.”. I come from one of the, for lack of a better term, preppiest parts of New England. Having gone to prep school myself, I say it is more a matter of personal preference rather than prep vs unprep. How does everyone else feel?

  16. Old Boston | May 17, 2012 at 12:18 am |


    Definitely a matter of personal preference.

  17. OB
    Personal preference or availability? Does anyone believe that due to geography or finances, even the most ardent could dress in J. Press clothing.
    While most get the origins of the clothing and give credit where credit is due, most through out this country buy what’s available.

    We forget that prior to the net and their expansion, the only opportunity to purchase Brooks Brothers was through trunk showings or catalogs.

  18. Personal preference, at least here in Boston where J. Press and Andover shops are practically in our backyards. These stores are the epitome of traditional style and sell both two and three button jackets.


    I will agree that most throughout this country are buying what is available.

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  20. elder prep | April 13, 2019 at 9:16 am |

    A fine guide to the correct lifestyle. Strong influence from the OPH.

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