Style Starter – Ivy & Prep

Covering the bare bones of the Ivy League look

Ben Keefe  |  May 12

Like the unified roar of an acapella group belting the last note at the social, Ivy style has been coursing loudly through the storied halls of the world's most famous institutions and has echoed far, far beyond. So far and wide, in fact, it has gotten lost in the day-to-day routine of getting dressed. That's because so much of what people wear today is based on, or has been influenced by the Ivy tradition without evening knowing it!

Perfectly capturing youthful ease and rigid tradition, nailing Ivy style - although taking much less investment than getting into one of the actual schools - requires more than just clothing. It requires a reverence for the style, knowledge of who wore it before, and of course the confidence and swagger to pull it off. 

Historical Context

19th-century engraving of Yale College via Getty Images

We'll get to the clothing in a second, but to fully capture the fascination with the Ivy look, one has to consider what the Ivy league stood for leading up to the surge in popularity.

Strongly associated with the beginnings of the US, the Northeast & New England house all 8 Ivy League institutions. 6 schools were founded in the 1700s and good old Harvard began in 1636, only 16 years after the first group of Pilgrims arrived at Plymouth Rock after traveling from England on the Mayflower. In this context, it's hard not to associate the Ivy League with enduring traditions that stand the test of time.

But beyond history, the tight-lipped, closed doors exclusivity of these schools created a culture where one's journey to get in starts long before the application process. Prep schools were where you'd go to prepare for the big leagues, often serving as pipelines to the Ivy League institutions.  As a result prep style was a more laxed, messier Ivy variant that mixed in athletic and casual clothing.

And just as a reminder, we are predominantly talking about the upper echelon of society here. So mixing the exclusivity, heritage, and wealth associated with the Ivy League, students could have been wearing potato sacks and they would have caught on - because the clothing was more than clothing and served as a symbol of success, backed up by the most famous schools and graduates in the world. And who wouldn't want to be a part of that?

The Kennedy Brothers during the 1960s. Image via Pinterest.

However, as Ivy league students and those peripherally in the mix wore the style to be associated with the rich histories of the institutions, it was only as it related to the trends of the time. As the trends changed, so did the dress. This is exactly why we owe the longevity of this snapshot of classic Ivy Style to the Japanese.

The Japan Connection

With the momentous "Take Ivy", Sohsuke Ishizu, Toshiyuki Kurosu, Hajime Hasegawa, and T. Hayashida took what was already happening at these elite American universities and framed it - validating it as a fashion trend with serious longevity through candid 'slice of life' photography. Of course, when the book came out in Japan, the kids went crazy. Especially those in the Ginza district of Tokyo. And it's not that wild to assume the kids going crazy for Ivy during the 60s were the first gen of Japanese buyers coming to the US in the 1970s to buy the current styles as well as second-hand clothes, releasing a wave of Americana that is still thriving today through the vintage, designer, and repro business.

Japanese teens in Ginza during the 1960s. Image via The Rake

This is where "W. David Marx's Ametora: How Japan Saved American Style" comes into play, outlining how the Japanese began doing Americana clothing better than we were. By keying in on the quintessential pieces and styles that the U.S. did so well -- but soon forgot about -- the Japanese were teaching us about what our parents, grandparents, and beyond were wearing and why it was so damn cool.

Although the longevity of the style can be heavily credited to our friends overseas, at the time American pop culture was pumping out subliminal and overt Ivy messaging from the actors on the silver screen and television to musicians and composers. It was further validated by features in national publications like Life Magazine which gave the public rare glimpses of the real thing.

Dustin Hoffman in The Graduate. Image via Pinterest

  Dissecting The Basics Of The Ivy Look

So, what is Ivy Style actually? In addition to being a symbol of acceptance and success in an ultra-exclusive club, the physical clothes represent tradition, ease, timeless style, rigid structure, versatility, and a host of other contradictory descriptors that somehow perfectly co-exist in equilibrium.

So, who are the main players? Let's dive in.

Oxford Shirts

Classic Ivy style exhibited by two Ivy League students, with a relaxed white Oxford shirt being worn by the gentleman on the right. Image via Ivy Style

If Ivy style was a house, the oxford shirt would be the foundation as the whole look builds on top of this iconic button-down. Traditionally coming in white and sky blue (the result of white and dark blue yarns being woven together in a

basket-weave pattern

), oxfords are a versatile garment that fits right into a suit, under a blazer, peaking through a sweater, and as the main event in a casual look with a pair of chinos, and loafers.

Gitman

has been making their Oxford shirts the same way, using the same materials as when they started way back in thre 1930s. If you know how hard it is to find an original oxford from the heyday of Ivy, this no-brainer is the next best thing.

Gitman Bros. Vintage Long Sleeve Oxford, $170 at

Shockoe Atelier

.

Short-Sleeve Button Downs / Pullovers

When the oxford is a hair too formal but the polo just doesn't feel right, a short sleeve button down in

madras

,

batik

, or a solid color does the trick. Especially popular in the spring and summer paired with khakis and loafers, the short sleeve button down would have almost always been tucked in creating a satisfying balance of relaxed and put together.

Japanese shirt Maker Kamakura has observed the Ivy tradition down to a to a tee and thanks to their attention to quality and cut, we have a chance to enjoy slept on staples of the time like this simple short sleeve button down that is all classic style and no filler.

New Vintage Ivy Short Sleeve Button-Down, $89 from Kamakura Shirts.Burgus Plus S/S Check BD Shirt, $120 from Sun House. 

Knits

Those Northeast winters can be unbearable without the right layers but dressing suave doesn’t need to take a back seat all the while. Knit sweaters and cardigans, worn over oxfords with or without a tie, is a combination that will last till the end of time. Finish it off with a blazer or suit depending on the chunkiness and you’ll manage to look sharp while staying warm and toasty.Enjoyed by Cary Grant, JFK, and hoards of stylish Ivy leaguers, the Shaggy Dog is the quintessential mid-century Ivy sweater. A complimentary shape with texture adds depth to any outfit without looking like you're trying too hard.Shaggy Dog Sweater, $245 from J. Press.The V-neck sweater and cardigan are also key pieces of knitwear in the Ivy style, as well as collegiate knits emblazoned with the school's initial i.e. 'P' for Princeton.Divison Road x Dehen 1920 Collegiate Cardigan, available exclusively from Division Road for $385. 

Chinos or 60s jeans

Pre-60s we may have been discussing more dress slacks and formal pants but when we are talking quintessential Ivy, khakis and later jeans are the swiss army pants that allow any outfit to succeed. Cuffed, lazily rolled, starched, pressed, wrinkled, not only can this complement or offset formal and casual looks, they work with any footwear - from oxfords, loafers, and moccasins, to pumps like Jack Purcells or Sperrys.O'Connell's is a traditional men's clothing store in Buffalo, NY that has been dressing the sharp-dressed since the late 50s. In addition to a selection of the best classic menswear brands available, their in-house label is comprised of well-made wardrobe staples that are clutch when it comes to style and construction. Their traditional plain front khakis which come in a variety of colors are a perfect example.O'Connell's Khakis, $135 from O'Connell's. 

1960s 501 Silhouette Jeans

The Levi's 501 is the archetypal 5-pocket jean, and although its lot number has stayed the same for decades, the actual fit has changed many times. After remaining a fairly wide-leg fit throughout its lifespan, Levi's tapered the cut in the 60s in line with ever-changing fashions. The 1966 Levi's 501 is often hailed as the key 60s 501 fit, and that's what Sugar Cane has reproduced with its SC1966 jeans.

Among all the 60s 501 repros, Sugar Cane's is a staple that is readily available year on year. Made from Japanese raw selvedge denim, it has a regular top block with a gentle taper through the leg.

Available for $220 from Franklin & Poe. 

Loafers

Vintage Alden Loafers via Etsy

If Ivy style had to narrow down its collective wardrobe to one footwear option, it would be the loafer and more specifically the penny loafer. The perfect ending to any outfit, the penny loafer in black or brown can traverse the very formal to the most casual somehow blending in perfectly no matter what the situation. Whether kept in their natural state or shined to perfect, they're impossible to mess up.

G.H. Bass Larson Weejun, $135 from G.H. Bass

The Bass Weejun. The loafers in all the old Ivy pictures you obsess over.  Although G.H. Bass has moved with the times, they've stayed loyal to what put them on the map and still carry their original models to this day. Dress them up, dress them down, loafers are going through a revival so you might as well get the tried and true. 

Rugby Shirts

Image via NAQP

Linked to the sport with the same name, Rugby Shirts are the 'rough around the edges' cousin of the polo shirt. Made from thick cotton and featuring long sleeves, rubber buttons, and a twill (often white or contrasting) collar, this shirt was originally a uniform that made its way into the casual dress lexicon. When layered, think less formal than a sweater, more formal than a sweatshirt.

Frizmworks Bold Stripe Rugby, $172

Wallace Mercantile & Shop

Athletic Cotton Tees

Under your sweater, oxford, or rugby shirt would have been a heather gray, navy, or white cotton undershirt sometimes blank, sometimes adorned with your school name, crest, or a phrase like ‘Phys. Ed’. This would be worn in the most casual of situations like playing an intramural sport or hanging out in the dorms. Although not as prevalent in Ivy as other garments until later on, when paired with penny loafers and chinos, you'd think t-shirts were born for this moment.Warehouse & Co. 2nd Hand Series T-Shirts, $75 from Clutch Cafe ($67.50 for Heddels+ members)

No one is doing the ink print athletic/phys-ed t-shirt like repro kingpin, Warehouse & Co. Nailing the cut, construction, and printing methods of t-shirts past, after a few wears this will be looking like a perfectly seasoned vintage tee. 

Soft Tailored Coats/Blazers

Image via Harris Tweed

Perfect for elevating a casual outfit, a soft-shouldered coat fits like a puzzle piece over a polo or oxford and pops when paired with chinos or a pair of jeans. Go loafers to keep it classy or fish out the dirty canvas sneakers to take the edge off.

Traditional Andover Fit Super 120's Navy Blazer, $675 from The Andover Shop

It doesn't get much more timeless - or closer to the source for that matter - than the Andover Shop's own blazer, an Ivy wardrobe staple that can make even the most uncouth looks look deliberate, keep things a notch below formal when needed, and rise to the formal occasion on when tapped. An investment piece that can pay off in so many ways. 

Final Thoughts & Image Gallery

Ivy Leaguer at the J.Press Store in New Haven. Image via Life Magazine

At its core, Ivy style is less defined by how ironed your shirt is, whether your khakis are pressed, or whether your blazer has a stain on it, and more by the fact that you're wearing it at all - the balance of rebellion and conformity. Worn in but worn well. A sharpness that doesn't rely on the presentation of the garments but on the quality, pattern, and the ability to pair it all together. That is Ivy. So study this guide, cram like heck and you'll surely pass the final. But for now off to the dining hall.

Image via Take Ivy

Image via Take Ivy

Image via Take Ivy

Image via Take Ivy

Image via Permanent Style

Paul Newman via The independant

Steve McQueen via Ivy Style

Ryan O'Neal & Ali MacGraw in 1970's Love Story via GQ

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