The Full Circle of Preppy

Actor Theo James on Nantucket GQ 684x1024 The Full Circle of Preppy

As with much of life, the modern aesthetic we refer to as “preppy” bears only a thin resemblance to the historical roots upon which it rests.  Often, the substance of a philosophy or belief is obscured over time as the surface decoration which was initially its outgrowth comes to define the entire idea.  The same can be said of preppy fashion.

It’s not too dramatic to state that the preppy fashion meme of today is but a shallow construct masquerading as some sort of cultural touch point.  The problem of course, is that preppy fashion has almost nothing to do with the culture it references, certainly not when it comes to actual, you know, culture.  However, as we move into the Spring of 2014, it would appear that designers are finally beginning to see the limits of the hyper-preppy overkill that has saturated the menswear space for several years.

The eye-burning excess of colors, patterns, crests, layers, skulls-emblazoned-on-everything, big plaid with little plaid with repp stripes, and velvet slippers to the office, finally seems to have exhausted even the most ardent of trend spotters.

So now, at long last, we can move onto the next phase in the ongoing preppy style circle of life.  As evidenced above in this relatively realistic GQ-styled take on preppy, a shift toward real life appears to be in motion.  Actor Theo James’ outfit, shot appropriately on Nantucket island, is thoroughly believable and wearable. Thank goodness.

The Influence of Real Life

Actual preppy style (that is, the preppy style of dress) evolved from life in New England preparatory schools, which by and large expressed conservative protestant values and social stratification.  Collectively, these influences created an environment which produced the uniform we know now as the preppy look.

Today, when someone is called (or calls themselves) “preppy,” it usually means that he dresses in a neo-traditional fashion, typically predicated on conveying a classically sporty lifestyle (crew, rugby, sailing, 1950s football, etc.).  Often, but not always, it is simply costume; no sense of history or understanding of the preppy culture.  That’s too bad, because actually, it’s a pretty interesting history.

Take Ivy Picture The Full Circle of PreppyMore so than other styles, preppy – East Coast, Ivy League, WASPy, call it what you will – has a real history behind it that clearly informs the fashion.

Perhaps that is why the style and implied lifestyle behind it, endures generation after generation.  While you can look polished and successful in a nice suit and carrying an expensive bag, you can convey many more social, cultural and status cues looking as though you just hopped off your Hinkley yacht after spending a week at the Cape house.

While for the most part it started at New England prep schools and ivy walled colleges, 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.

A culture of thrift and purpose also pervaded the Ivy League world.  Clothing was worn until it frayed, upon which it was patched and sewn.  Garments were handed down and cherished, signs of age and wear denoted a certain authenticity and personality that only time conveys.  Preppy style looks so good because it looks so worn and beat-up, lived in, and loved over time.  This focus on These

This environment helped create a culture of exclusivity that had real influence.  To say you prepped at Phillips Exeter (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.

From Exclusive to Popular Culture

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.

Kennedy Short Khakis The Full Circle of PreppyWithout question, it was an exclusive, self-impressed, and privileged world that gave birth to preppy style and the culture that underpinned it.  But, as with so many other attempts to create a homogenous 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 arbiter 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.  It was, and remains, the de facto guidebook to being preppy.  And, while she issued a follow-up, “True Prep” in 2010, the original remains unquestionably dominant in influence.

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. In that moment, the life of prep was effectively democratized. That is because once the Preppy Handbook came out, kids across the world latched onto the single most attractive and achievable aspect of the actual preppy’s life: its look – the rumpled and ironic blending of dress and casual clothes.

Ralph Lauren Preppy The Full Circle of PreppyIn the intervening years, preppy style has been interpreted, parsed, watered down and ginned up to such a degree that for many it has been commoditized beyond recognition.

In response, sites like Christian Chensvold’s Ivy Style launched as a sort of counterbalance, reminding people that this preppy fashion thing actually had a rich and important story behind it.  Yes, anyone can dress preppy, but “being” preppy is actually something altogether different.

When we first broached this subject years ago, one OTC reader pointed out that what some only know of as iconic Ralph Lauren branding, the mixing of dress and functional clothing, did not actually start out as a fashion movement.  His comment was in itself an expression of true preppy-ness:

“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 this 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 the aforementioned Ralph Lauren.  Over time, the prep boom of the 1980s waned due to its extreme and vibrant interpretation of the preppy culture – the same issue facing the trend today.  At its apogee there was an almost cartoonish quality to the movement.  Sound familiar?

Finding Preppy’s Roots

What we see moving into the American preppy space now is an interest in a more reality-based look; muted colors and less overt branding and styling, singular pops of color rather than a cacophony that overwhelms.  Less “look at me, I’m preppy!” and more “oh, this old thing was my dad’s when he was in school.”

Hopefully, all this will translate into a more careworn, comfortable and vintage preppy personality; approachable and less precious than in the last few years.  Many of the style’s adherents are now looking for a little substance behind the flash, the story behind the fashion, and a more accurate read on the overall Ivy League look.

How wonderful would it be for the renewed focus on menswear quality, detail, provenance, and longevity to extend to the history and culture behind that most American of fashions?  Let’s make understanding the roots of American preppy as stylish as dressing in American preppy.


Nantucket Brand’s Half-Zip Sweater

0054 Nantucket Brands Half Zip Sweater
The tiny but enchanting island of Nantucket has long been a magnet for lifestyle and aspirational brands.  The handsomely rugged location and windswept geography, combined with the island’s historically East Coast patrician aesthetic, make for an irresistible backdrop.

Apart from the Kennedy compound-ish positioning that often accompanies Nantucket themed marketing or product shoots, the island has a deeper and more appealing personality that we really admire: hardiness.  While there is certainly an ever growing contingent of millionaire and billionaire residents snapping up prime land for their Gatsby-worthy estates, as far as we are concerned, the time-worn functionality of everyday hard working essentials holds far more character and style.

Nantucket Brand Logo Nantucket Brands Half Zip SweaterAnd, for that reason, OTC is particularly fond of Nantucket Brand’s navy half-zip pima cotton sweater.  It is a classic layering sweater in the best of ways.  Simple and well-made, functional, pragmatically stylish, and it works with a variety of outfits in different seasons.

We’ll be the first to say to that the website’s pictures do not really do it justice, which is a shame.  However, once in hand, it quickly became a favorite and has been regularly put to use in both dressy and casual situations.  We like to pair it with jeans and a simple tee shirt or khakis and an oxford cloth button down.

The soft cotton has a mid-weight sweatshirt quality to it while the unique rounded standing collar, worn up or folder down, provides a signature and somewhat vintage feature.  The self colored YKK zipper seems to disappear into the sweater and in doing so gives it a cleaner, simpler look.

The Nantucket Brand company was founded in 2005, and built on a family history with ties to Nantucket stretching back to 1945.  In addition to the website, the company has three Nantucket-based shops and product ships from either the island itself or the equally charming and historic New Bedford, Massachusetts.

0060 682x1024 Nantucket Brands Half Zip Sweater


Read Wall’s Clean American Prep

Read Wall Roosevelt Oxford 1024x682 Read Wall’s Clean American Prep

Simple lines and details that are both functional and aesthetically relevant are the rule when it comes to Read Wall’s clothes.  For example, his oxfords are trim but not skinny, and have a unique feature that speaks directly to his grown-up sense of American style; a flapped chest pocket.

Some designer like shirt pockets, others opt out.  The flapped pocket on Read Wall’s shirts is a direct homage to the classic J. Press oxford.  To us, that kind of nuanced historical referencing – and the clean, modern way the detail is executed – is the sign of an intellectual designer’s mind.

Read Wall Logo1 Read Wall’s Clean American PrepIn some ways, Read has no right to so effectively employ this stripped down, mature East Coast aesthetic.  At a mere 26 years old, one might expect this young designer to be following the overblown faux old-world preppy trend, but no, he’s past that.  Form, function, and offhanded class are core elements to the brand.  Another driver is a commitment to creating true American sportswear; the kind that JFK effortlessly employed with great wind swept success.

Even his name, Read Wall, (yes, it’s really his name) reflects the brand’s mature WASPyness.  It’s classic, clean and unique in a way that catches your attention.  His clothing could be similarly described; simplified modern classics.

Read Wall also trades on its construction and materials.  Fabrics are individually sourced from top mills in Japan, Italy, and the United States.  And, holding true to the American-ness of the brand, all their products are manufactured in the U.S., in factories focused on a particular expertise.  The shirts are made by actual shirt makers, trousers by pants experts, and now suiting by one of the best (and last) large-scale tailoring shops in America.

Read Wall Wright Chinos Detail Read Wall’s Clean American Prep

Speaking of pants, Read Wall Wright Chinos are flat-out awesome.  Clean lines create a trim but comfortable silhouette and the dense brushed twill is perfect for the coming autumn.  Dressier details like the buttoned fly and extended tab waistband give them a personality that can go formal or casual with ease.  And, although the website’s product shot don’t really show it, the 7.5 inch leg opening provides a pleasingly modern taper.

Currently, you can find Read Wall on the web, but plans may be in the works for a physical retail presence.  Read Wall has already received a great deal of positive press and the reviews reinforce his approach and aesthetic.  So, whatever the next steps prove to be, they should look pretty good.

Read Wall blue ging ox chino 682x1024 Read Wall’s Clean American Prep

Read Wall Red Oxford 682x1024 Read Wall’s Clean American Prep

Read Wall Lead Shot1 Read Wall’s Clean American Prep

Read Wall Waxed Jacket Green Read Wall’s Clean American Prep

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Read Wall Waxed Jacket Read Wall’s Clean American Prep

Read Wall Navy Oxford 682x1024 Read Wall’s Clean American Prep


Tactical Style: TAD’s Stealth Hoodie LT

TAD Stealth LT 1 Tactical Style: TADs Stealth Hoodie LT

Triple Aught Design (TAD) is a really unique brand.  It’s products are grounded in a tactical, purposeful world.  Function first and form second; the mantra of a company that seeks to create products and garments that last and perform.

As a brand that is quality- and detail-driven, we find their products to be very much in the true preppy ethos; built to last, perform an outdoorsy function, be unique, and meant to be used, not simply admired.  So, while there isn’t a repp stripe in sight, the preppy DNA behind TAD’s Stealth Hoodie LT is front and center.  It’s not meant to simply look tactical and rugged, it is tactical and rugged.

And, to us, that’s what actual classic style embodies; adopting something for day-to-day life that has inherent style but is purpose-built.  Take a good look at old-school preps. They have stuff that really is old, re-purposed, beat-up, frayed around the edges, and not from a brand that makes stuff to just help you look like you are old money.  They like things that work and that last, that are generally neutral in design and posses innate value and longevity.  They don’t want 10 raincoats; they want maybe two.  One that works well with a suit and is appropriate for the office and another one that can go from the boat to the trail to the grocery store.

This is the latter.  The TAD Stealth Hoodie LT is built to last forever and has a wonderfully functional style that appeals to our pragmatic New England-ness.  This lightweight version of the Stealth jacket is trim and no-nonsense in the design department and also has a ton of useful pockets in unusual yet perfectly sensible places.

Zippered underarm air vents allow for cooling and the chest pockets have integrated openings that allow you to snake your headphones up through the inside of your jacket, keeping cords out of the way and favorite podcast close at hand.  Even the zippers have clever “hoods,” so when they are closed, no water or wind will slip inside.

To learn more about the many overbuilt and totally weatherproof details that make up the Stealth LT, take a look at the TAD website.

TAD Stealth LT 4 Tactical Style: TADs Stealth Hoodie LT

TAD Stealth Detail 2 Tactical Style: TADs Stealth Hoodie LT

TAD Stealth LT 5 Tactical Style: TADs Stealth Hoodie LT

TAD Stealth LT 3 Tactical Style: TADs Stealth Hoodie LT


Concord Button Downs2 Concord Button Downs: The New Old School ShirtIt should come as a surprise to no one that far too often form trumps function in the fashion world.

Creating something in the “style” a timeless classic is more important than actually creating something that will last long enough to become a classic. “Inspired by” is often a phrase that makes our warning flag go up.

Take the humble but indomitable oxford cloth button down shirt, “OCBD” to the preppy cognoscenti. It is perhaps the quintessential American garment, regardless of the fact that it was in fact brought to America by John E. Brooks, as in Brooks Brothers, in 1896. While taking in a polo match, Brooks was captivated by the non-flapping shirt collars worn by the English polo players. To prevent them from being whipped in the face during full-speed gallops, the riders’ collars were held in place by small buttons.

Brooks took the concept back to the States and created his own version. Thus was born the legendary Brooks Brothers button-down polo collared shirt, perhaps the most famous version of the now iconic garment.

While Brooks’ OCBD is perhaps the emotional standard-bearer of the trad-iest of all Trad garments, it is not necessarily perfect, or for that matter, what it once was. Taking this as a starting point, Dan Castelline, founder of Concord Button Downs set about the task of creating a seriously old-school, like-your-dad-wore OCBD.

Constructed from 100% untreated cotton oxford cloth, these shirts are meant to be passed down father to son and worn into the ground. Founded in Concord, Massachusetts, Castelline sought out local seamstresses to cut and assemble the shirts.  While the fabric is imported, all production is not only kept in America, but also kept in New England.

To ensure that each shirt meets specific criteria, a 65-step process covers every detail of construction. By incorporating old-school characteristics found in traditional prep school attire with updated shirting details and silhouettes, Concord Button Downs’ shirts reflect a modern take on this wardrobe staple.

While the overall cut is traditional, extra fabric has been trimmed from the waist and hips, eliminating the typical blousing effect of a full-cut shirt. The result is a trim fit that is neither slim nor skinny, but realistic and comfortable.

Collar points have been slightly lengthened to achieve a more balanced look and the collar itself is constructed without interlining or fusing. This creates a shirt collar that is soft and able to form a natural full roll. Additionally, each collar is attached by hand. Together, these elements allow the collar to be “turned” once it reaches a well-worn and frayed state, should you choose to keep it fresh looking. Now that’s New England sensibility for you.

Concord Button Downs Logo Concord Button Downs: The New Old School ShirtThe distance between the collar button and second button was also increased, which presents a more natural look when not wearing a necktie.

While there is no visible logo up top, the company does make a clever and subtle concession to branding that we happen to like. Their Minuteman emblem is stitched on the bottom of the shirt’s inside placket and is visible only when the shirt is worn un-tucked.

We love these shirts, and while we hope that sizing will eventually expand to neck/sleeve gradations, for us, Medium is just right. They are not inexpensive, but these OCBDs are meant to be a lifelong investment, and when viewed in that light, $128.00 is a deal.

We also want to add that on a personal note, Dan is an impressive young guy. Starting your own business at a young age is one thing, and actually getting a foot into the garment industry is another one all together. But talking on an iconic and frankly interchangeable product like the button down oxford takes some guts.

In our opinion, Concord Button Downs has indeed succeeded in crafting a shirt that you should have in your closet. Actually, you should have several of them in your closet.