In Praise of the Preppy Look

In Praise of the Preppy Look

The Ivy League look is on all of our radars: but how many of us actually try and achieve it? Ask most gentlemen how to dress, and theyll probably opt, almost by default, for impeccably tailored, boardroom friendly chic: Sean Connerys Bond in his more sober guises, perhaps, or Marcello Mastroiannis photojournalist protagonist in La Dolce Vita. The plaid three-piece bravado of Steve McQueen in The Thomas Crown Affair is perhaps a more flamboyant outlier.

But wouldn't it be fun to embrace a breezier, sportier take on timeless sophistication? And, when the mercury rises, wouldn't it be more appropriate to dress in ensembles better suited to the promenades of the Côte d'Azur than the corridors of Wall Street?

What Is Ivy League Style? 

Essentially, it’s a lasting tribute to the casualization of traditional style tenets, which originated in decades yore on the more prestigious college campuses of the Northeastern United States.  You may remember Jude Law, flawlessly dressed in The Talented Mr. Ripley—with his half-open knit polos, pleated white shorts, linen blazers, and white loafers. The film, nominated for five Academy Awards including Best Costume Design, showcases his character Dickie Greenleaf and his iconic playboy lifestyle.

Robert Redford in Barefoot in the Park – think button-down shirts, diagonal-striped ties, blazers and that neat side-parted haircut – exemplifies the more “Trad” area of the field, as does James Coburn’s character (seersucker jacket, Persol sunglasses) in The President's Analyst. If you want to turn the preppiness up to 11, you might want to check out the emerald-green shawl neck cardigan/bowtie combo worn by Tobey Maguire in The Great Gatsby.

Great Gatsby green cardigan

And if real-life style icons are more compelling to you than fictional ones, consider John F Kennedy: the 35th POTUS and his family were the first to be willingly photographed off duty, which has furnished the world’s picture archives with stunningly evocative shots of Kennedy and his clan in crew neck sweaters, khakis, swish sneakers and wrinkled oxford shirts.

Preppy Style: An Origin Story

So how did The Ivy League style movement (and its cousin “preppy” style, a playful nod to the preparatory schools that affluent families sent their children to) all begin? And how has it defied the basic principle – as much of a truism as that which dictates all empires must fall – that all style movements must eventually expire?

Alan Flusser, designer, tailor and author of Dressing the Man: Mastering the Art of Permanent Fashion, once told this writer that the story goes back to the late-1910s and early 1920s. “Arthur M. Rosenberg was, at the time, considered the best tailor in Newhaven,” he said, “and there started to be this experimentation around Yale undergraduates based on a new, free-thinking, a more casual manner of dressing – and he started to make clothes for this movement.”

scent of a woman preppy style

The campuses of Harvard, Princeton and Yale may have given birth to the look: but it inevitably spread all over a region encompassing The Hamptons, Martha’s Vineyard, Nantucket and anywhere else awash with old money. Hence, Ivy League style’s strong sport and leisurewear element deriving from activities favored by wealthy families – notably polo, sailing, hunting, fencing, crew rowing, lacrosse, golf, cricket and tennis.

Now, the Ivy League guise has gone global. And for that, one man can be credited more than any other. “People ask, ‘How can a Jewish kid from the Bronx do preppy clothes – does it have to do with class and money?’” Ralph Lauren once asked. “It has to do with dreams.” Over to Flusser again. “Without Ralph Lauren, there would probably be no Ivy League dressing as we know it now,” he told me, referring to the way the most successful American fashion designer of all time re-popularised Ivy League apparel such as polo-player logos, blue blazers, white denim, repp ties and so on.

Prepping The Look

And so, over a century after the look was birthed, it is a truth universally acknowledged – to borrow from Jane Austen, in keeping with the scholarly theme here – that a man in pursuit of a timeless wardrobe must be in want of some decent Ivy League staples. Happily, Anatoly & Sons is awash with options.

Knitwear is fundamental to the look: shawl collar sweaters and v-necks are both conducive to preppy-style layering, whilst turtlenecks such as our cable knit sweaters also ramp up the preppy permutations your wardrobe can throw up. Oxford shirts – especially in pastel hues –  are another vital ingredient (consider wearing them beneath a sport coat, with a splash of color courtesy of a silk pocket square). Loafers, tassel or plain, help ensure you nail the look literally from the ground up.

Lighter coloured trousers – such as these pleated cotton twill chinos in beige  - are a must, as are polos: especially in lighter colors such as our linen polo in mint or our cotton knit polo in an elegant cream. And, if you really want to go into preppy overdrive consider adding this silk grenadine bow tie in a rich merlot hue for some dashing, Pitti Uomo-worthy sartorial panache.

All of which showcases, in all its glory, some great news: mastering the Ivy League look with flair is not that difficult. A movement which was born of period elitism is now perhaps more accessible than any other sartorial genre on the planet. Or as The Official Preppy Handbook author Lisa Birnbach puts it, “It just so happens that almost anyone can assimilate into our world of prepdom. The desire to be prep is the most important factor.”

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