The Roots of American Preppy

This column grew out a discussion on my blog, Off The Cuff DC, on the relationship between classic and preppy styles. The subject quickly became an effort to identify the real roots of American preppy and what it means today.

New England preparatory schools, conservative protestant values and social stratification all combined to create an environment which produced the uniform we know today as the preppy look. Actually, what passes today as “preppy” is a fantasized ideal of make believe history. It is a manufactured past that distorts the classically rooted values which gave birth to the preppy culture. When a kid is called a prep today, it usually means that he wears rugby shirts and shops at Abercrombie & Fitch (I remember when A&F was, in fact a great store). There is no sense of history or understanding of the preppy culture and that’s too bad, because it’s a pretty interesting history.

Yes, it started mostly at New England prep schools and ivy walled colleges. But the roots of preppy style can also be traced to a focus on social achievement, uniformity of style, propriety, proper decorum and class distinction. Conformity of dress at school resulted in the basic uniform of coat, tie, button down shirt, grey flannels or chinos and loafers or lace ups. Codes, traditions and sports also helped to nurture a bond and familiarity among budding preps and instilled in them a feeling of belonging.

This environment helped create a culture of exclusivity that had real influence. To say you prepped at Andover (a feeder school for Harvard) or Hotchkiss (a feeder school for Yale) could win you access to the right social circle or get you into really great parties. And once in the working world, to say you were a Yale man could mean getting the right job, joining the right club or vacationing on Martha’s Vineyard.

As preps sought to instill that sense of tradition and lifestyle in their own children, they looked, of course, to their own preppy past. To the oak paneled lecture halls of Exeter, the squash courts of Deerfield and the rowdy but stylish nights at Choate Rosemary Hall. So their offspring were trucked off to the old alma mater and the cycle began again. But, as with so many other attempts to create a bubble of exclusivity, the prep school aesthetic eventually moved beyond its original sphere of influence.

People want what they do not have or what seems more attractive than what they do. So, when the Preppy Handbook hit the shelves in 1980, its editor Lisa Birchach (herself a Brown grad) overnight became the arbitrar of all things pink and green. People didn’t care that it was intended to be both a send-up of the “true” prep culture as well as a tongue and cheek education for those looking to emulate the life. They saw a way of living that was far more exciting, cultured, sporty and stylish than their own - and they wanted it.

For the first time, preppy culture had been distilled into a portable and easy to understand resource. The privileged and windswept lifestyle that had taken generations of Blue Bloods to develop and refine was now a commodity to be bought and imitated. I often use the term “democratization,” to describe this moment in the life of prep. That is because once the Preppy Handbook came out, kids across the world latched onto the most attractive aspect of the preppy life: its look, the rumpled and ironic blending of dress and casual clothes.

As one of my readers sharply pointed out though, the iconic Ralph Lauren image of mixing dress and purposeful clothing did not start out as a fashion movement; “you don’t wear foul weather gear over your blazer because you’re a blue-blooded American demonstrating your accessibility without appearing tacky; you do it because you’re a wise-mouthed elitist who smugly tells your Latin professor, technically speaking, you haven’t broken any rules so there’s nothing he can do about it. And of course it’s sailing gear, because your father does own a yacht…”

The original audience for the rebellious “foul weather gear over the blazer” look was other preppies and their families. Yet, as this type of hybrid style came into its own, it seeped out into regular society. Eventually spreading to Madison Avenue, it was popularized by style influencers like Ralph Lauren. The prep boom of the 1980s waned over time due, I think, to its extreme and vibrant interpretation of the preppy culture; there was an almost cartoonish quality to the movement. Broadly speaking, the current resurgence in preppy style has taken on a more worn, comfortable and “vintage” personality. It seems approachable and less stuffy.

An interesting thing has happened to the breeding grounds of prepdom too. If you walk through Harvard Yard or Yale’s Old Campus, you don’t see too many of the snooty old-line preps anymore. They are still there of course, along with Skull & Bones and the legacy kids whose wealthy parents bought their admission. But what you really see is that a majority of the kids milling around campus these days more closely reflect the modern world. The prep thing is still very strong – stronger perhaps than in the 1980s – but it has been modernized and updated. Just like everything else in life.

Polo Shirts, Rugby Shirts and “a Little Imagination”

“A little imagination” my dear old grandmother tells me “goes a long way.” Of course, she was right, although I am slightly piqued that my overly fertile imagination has frequently left me high and dry in the realm of dreams whilst my companions, keen to step ahead, have wisely pursued their manageable ambitions in the doldrums of reality. If necessity is the mother of invention, then imagination is surely the rather caddish father; for where would modern transport systems be without the imagination of people like Isambard Kingdom Brunel or music without Bach. I stand by imagination as something fine and cerebral. It sets one out from the crowd.

Indeed, setting yourself apart from the crowd is possible with even the most basic of apparel. The polo shirt and the Rugby shirt; simple and innocuous, if a little dull, are two favourite items of clothing for the spring wardrobe. Technically speaking, they constitute ‘sportswear’ since they were designed and made for sport. However, you’re just as likely to see either one worn on Fifth Avenue as on the field of tourney. They are accepted as being ‘slightly smarter’; more preppy and dare I say elegant, at least in comparison to the nylon shorts and tracksuit tops that bulge from the sportsman’s wardrobe. You could wear these items rather simply: over t-shirts with casual khakis or denim and deck shoes or you could impress women like my matriarch of a grandmother with more imagination.

Polo shirts

Though the polo shirt is definitely not something to wear formally, it has certainly upgraded itself year after year, no small thanks to retailers like Lacoste and Ralph Lauren who do battle each summer on the terracotta breakfast terraces of luxury hotels (to me, nowhere has there been a more palpable sense of competition between these mighty brands). They are generally worn rather slovenly, with swim shorts and flip flops in the summer or sweatshirts and jeans in the spring. However they look at their best when assisted by blazers, smart trousers and vests. It’s very important that the polo shirt is clean, crisp and fitting; baggy shirts under smart jackets look abominable and it’s a good idea to keep it plain. Another tip: use the collar. It’s oh so chic when the polo collar is worn outside the blazer.

Another unconventional look for the polo shirt is, come summer time, wearing it with a slim tie. Though this sounds like a mismatch of styles, it can come off very well although it is important that the polo shirt is a slim-fitting shirt and that the tie is also plain and very slim – fat kipper ties look absurd with polos. Worn correctly with some short tailored shorts and some sleek loafers (no socks of course) and an unbuttoned cardigan, it looks alternative, original and yet instantly classic.

Rugby shirts

Thick, hardy and comfortable – the Rugby shirt is not exactly the customary addition to the style man’s wardrobe, but it is for more casual looks and like the polo, it has heritage in use and design. Retro sportswear is everywhere this spring, as it has been for the past few years so the very English, very preppy Rugby shirt would be a sensible purchase. In England, Rugby fans frequently wear them short sleeved with the logos and sponsors emblazoned on breast and arm; rugby of old was far more minimalist in terms of adornment – Ralph seems to have the right idea on this one: simplicity and classicism united, the only adornment is a number or two, the trademark pony or a very elegant crest.

Normally they are worn on their own, or worn over white t-shirts with jeans or chinos, which is certainly not an unpleasant look, but easily bettered. Wearing a striped or checked shirt with a plain Rugby shirt is charming, especially if shirt cuff is also on display and adding a crested tie or even a bow tie takes the ‘rugger’ to that next level; no longer is it a humble item of leisurewear, for being seen in the same company as silk dicky bows and ties, it receives accolades and respect. Wearing some slim fitting dark blue un-faded denim and some penny loafers puts a bit of Harvard Yard chutzpah into this ‘English heritage’ ensemble.

Designer vs. High Street: My View

Ideally, buying designer clothes should be about design.

Runway shows have a perennial fascination because they showcase (in rapid, often dazzling procession) a series of unique and original designs. They are a flick-book approach to art – glimpses into the mind of a designer with one theme, and perhaps hundreds of preoccupations.

The best designer stores, equally, are fascinating. Glancing through rails, even just taking in the mannequins and their lighting, pose, dress, can be an aesthetic pleasure, akin to any exhibition of design. One walks out the best of them feeling inspired (even if you couldn’t afford anything inside).

But many designer purchases are about three values, only one of which is design. Those other two values are branding and quality.

When making such a purchase, bear in mind which of those three values you are prioritising and why. This will help you decide whether to opt for that designer bag or its high-street equivalent.

Branding
The first value, branding, can be dealt with most easily. Everyone succumbs to it to a greater or lesser extent – the desire to belong to that view of life, that aesthetic, to buy into it and possess a part of it. While this is objectively the least rational value, it would be churlish to condemn it. And without it life would be a little duller. Buy into it if you want, but be conscious what you are doing.

Quality
Buying something for the quality of its workmanship is far more rational. It will last longer, and look smarter for a greater proportion of that time. In the case of classic men’s clothes such as suits and shoes, that quality will mean something lasts for a decade rather than a year.

Designer clothes will be better made than high-street ones. But the difference may not be as large as you think. Many suits, for instance, are made in the same factories for different brands – one buyer told me that Austin Reed, Aquascutum and Gieves & Hawkes suits are all made in the same factory despite representing high street, designer and tailoring in many people’s minds.

Some of those suits are only super 100s or below, and fused rather than canvassed. Designer doesn’t necessarily mean quality. Research the brand and know what you are buying if you want quality – Mulberry bags, for instance, are designer and they are still made in England and will last a lifetime.

Design
Design has value when it’s unique. So buy designer clothes for their design when you can’t find them anywhere else. As with much in this posting, this has an echo in Winston Chesterfield’s thoughts last week – I would pick out his sunglasses example as something that can easily be copied, and so found on the high street. Buying a designer version seems pointless. You are not buying it for design or for quality. It’s all about value number three: branding.

Other examples of pieces that can easily be copied are belts, hats, ties and socks. You may buy a designer version of this for its superior quality, but not for its design. The pieces that are worth buying for their unique design are those that are complicated: suits, dresses, jackets, shoes. They are unlikely to be copied well.

So, in answer to the question of whether to buy high-street or designer clothes, I say: analyse where the value is. Is it in design, in quality or just in branding? Thinking through those three should make the decision easy.

Right Way to ‘Do’ a Three Button Suit

Whatever happened to the three button suit? It really doesn’t seem that long ago that the normal suit; the veritable ‘everyday potato’ of suits came with a trio of buttons. I must admit, when it was everywhere, I yearned for the individuality, not to mention the elegance, of a two button suit. To me, there was something a little off about the recent three-button suit: being worn with the two top buttons done up, with awkward lapel shortness. It lacked the dignity of a low-break jacket like a one or two button. To me, two-buttons epitomised the élan of St James’ but a three-button merely reminded me of an extra from the set of Ricky Gervais’s ‘The Office’; the fat shapeless tie underneath, the terrible cuts and the ubiquitous ‘strait-jacketing’ – the preponderance of fully buttoned-up suit jackets. It looked like the sartorial equivalent of an industrial estate.

Now of course, the two-button suit is everywhere and yes, it has been ‘ruined’ by ubiquity and inelegant adaptation. However, it is still the suit I favour. This is largely because, for those with off-the-rack tastes, it is very hard to get it wrong. The low break of a one or two button jacket means that more of a man’s shirt and tie is on display, which offers a pleasant frankness to an ensemble. There is a sleekness to the cut and yet also a schoolboyish charm. The three button is precisely that; more buttoned up. The shorter lapels detract from the potential elegance of a suit; it seems, looking in the mirror wearing a three-button jacket, too restrictive. This is, of course, because it has been made, and indeed because I am wearing it, in the wrong way. There is actually a right way and a wrong way to ‘do’ a three button suit.

Buttoning

Firstly, I think it is far more elegant when only the middle button is secured on a three button suit. When the top one is also secured it looks, frankly, wrong. If the jacket is fitted enough (see below for ‘Fit’), then an attractive ‘X’ shape should be created when wearing the jacket with the central button fastened. This means the jacket ‘breaks away’ appealingly at the bottom rather than falling mundanely ‘straight.’

Fit

The second thing of importance is, naturally, that the jacket fits properly. Too many three button jackets are worn loose, without character. It wouldn’t do well to purchase a very slim fitting model; despite not using them, one should be able to button all buttons without any stretching on the material or strain on the buttons. The reason for this is that the jacket will eventually lose its shape if the tension is too great.

Personality

The last thing that is crucial for the jacket is the element of personality. Cary Grant used to wear his three buttoners with ‘lapel-plus’: folding the top button and button-hole over, adding to the overall length of the lapels. While one wonders why he did not simply purchase a two-button suit from his tailor, it becomes apparent that such individuality and idiosyncrasies make the suit something special. Grant’s affectation turned a many-buttoned suit from something Victorian and prim into something sporty and modish.

If You Own One Suit

Maybe you are about to graduate college and you need the one suit that will get you through all your job interviews or perhaps you just want to clear out your closet full of boxy, outdated suits, the solution for either case is a modern, versatile suit that will fulfill all your needs.

The current trend in suits has been towards a mélange of 90’s era minimalism and the modern-day obsession with slim.  This present infusion has reached the pinnacle of style in achieving a timelessness and wearability that means it will look as attractive in ten years as it does the day you buy it.

The two most versatile colors for suits are either gray or navy, with gray being the more fashionable choice.  A light-wool, gray suit is the best option because it’s like a blank canvas—anything can be paired with it, allowing more outfit variations with less investment.  Black is also permissible, though it is sometimes considered too ‘flashy’ for certain job interviews.

The trousers should fit snugly around your waist and should be tapered to your leg.  When buying an off the rack suit, it is imperative that you bring it to a good tailor to have it fixed for your body.  A flat front pant will make you look slimmer and is the most modern choice.  If you want a slim leg, which is currently in style, do not hesitate to be explicit in your desires.  Sometimes in more conservative establishments, a tailor may be apprehensive about bringing in the leg too much.  The break and cuff of your pants is highly personal and dependent on your tastes, but if you own only one suit, it’s best to leave the bottoms uncuffed with the trousers ending just above where the heel of the shoe begins.

The jacket, like the pants should outline your body without restricting movement.  The waist should be darted, meaning that it hugs and gives shape to your torso.  Opting for a two-button is a good way to subtly distinguish yourself among a sea of banal three-buttoned suits.  While peak lapels are currently fashionable, a safer bet is a traditional, but slim notched-lapel.

A reasonable range for a first suit is between $500 and $1,000, though it is not impossible to find something for less.  A smashing suit can potentially be a deciding factor of whether you get the job or the girl—or a job from the girl, so investing in a good one is key.