Preppy Style Aesthetic: How To Dress The Modern Preppy Way

With a combination of collegiate classics, relaxed tailoring and contemporary streetwear, the preppy aesthetic is a style we can all get behind.

Words by: Ryan Thompson

Who would have thought that an aesthetic with its origins in British college rowing clubs from the early 20th century would have evolved to become the style du jour in menswear? That is exactly where the modern preppy look came from, notwithstanding a hugely influential detour to the US east coast in the 50s and 60s.

Preppy style, characterised by a marriage of varsity nostalgia, casual tailoring and vintage-inspired sportswear, has at its core a playful if not slightly nerdy vibe that’s easy to style with most elements of a modern wardrobe. It has more recently been brought to the forefront of fashion followers thanks to the likes of Alessandro Michele at Gucci, who has interpreted his own maximalist version.

Newer cult streetwear brands such as Aimé Leon Dore have further propelled the look that was once the reserve of middle class white guys to a diverse global audience. To get the look right, you need to dig into its origins to understand how all of the different elements tie together, so let’s get started…

What is preppy style?

Photo of vintage Men's preppy style from Take Ivy book

Take Ivy

Although we associate the genesis of today’s preppy style with the campuses of Ivy League universities in the 50s, the true origins can be traced back to the collegiate rowing clubs of mid-19th century England, where oarsmen wore brightly coloured jackets in order to be discerned by the crowd on the river banks. Later, students attending social functions would wear their rowing blazers in an act of youthful sartorial rebellion.

The blazers were often striped to differentiate one club from another. It wasn’t until the early part of the 20th century that the look caught on with university peers across the Atlantic, but by the 1950s, the ownership had been wrested away from Oxbridge and was creatively evolving in the elite corridors of the Ivy League. It symbolised moneyed, well-heeled, upper-class privilege, and was famously parodied in Lisa Birnbach’s seminal books, The Official Preppy Handbook and True Prep.

Photo of vintage Men's preppy style from Take Ivy book

Take Ivy

The sporting influence did not get lost in transatlantic translation, as pastimes such as polo, sailing, tennis, rugby, golf and equestrianism all informed the preppy aesthetic. It was also, still, a mode of rebelliousness, as students took elements of their fathers’ wardrobes and subverted them with a casual sports aesthetic that used bold colour contrasts and vibrant patterns such as Madras check in what was perhaps a bid to differentiate themselves from the charcoal suits of the cubicle drones of white-collar America.

How the preppy aesthetic evolved

Modern men's preppy style aesthetic

Rowing Blazers

The fact that preppy style hasn’t significantly changed since the 50s tells you all you need to know about its timelessness. As one of the most referenced 20th-century menswear movements, it has popular culture to thank for much of its evolution over the decades, from JFK and Miles Davis in the 50s, to the Beastie Boys in the 90s and Tyler the Creator today.

In a sense, it has always been modern, because it has incorporated elements of tailoring, vintage, and sportswear no matter what the decade, but more recently it has had a contemporary shot in the arm thanks to certain brands like Noah and Rowing Blazers who have introduced a more urban aesthetic to the melting pot.

Gucci, too, has been exploring a maximalist approach to preppy style since Alessandro Michele took charge as Creative Director in 2015, further propelling the look to a global audience. Its modernity then is all wrapped up in its diversity and versatility, giving us any number of ways to pull off the look.

How to dress preppy

Stripes

Whether it’s the collegiate stripes on a sports coat, the thin blue lines of a Breton, or the subtle pinstripe of a seersucker suit, the preppy uniformity of stripes can add a colourful contrasting dimension to the look. The stripes have their origins in baseball, which in turn were borrowed from British bankers of the early 19th century who wore certain styles of pinstripe suits to help identify which bank they worked for.

A striped Oxford Cloth Button Down (or OCBD as they are known) can be a simple yet very effective way to introduce the pattern into your wardrobe since you’re able to wear it with relaxed tailoring on the one hand, or have the collar peeping out of a cotton sweatshirt on the other. Think pastel stripes in the summer, while in the cold months opt for darker shades with greater contrast.

Varsity jacket

The varsity jacket, aka ‘letterman jacket’, is an icon of collegiate sports style, immortalised by Emilio Estevez in John Hughes’ cult classic The Breakfast Club. The tradition of awarding sporting high-achievers with letters (often the initial of the college) to wear on their jackets harks back to the Harvard University baseball in 1865, although back then they were embroidered onto sweaters.

The varsity jacket silhouette is typically that of the iconic MA-1 flight jacket with a ribbed elasticated collar and often with contrast-colour sleeves. It’s an iconic piece of collegiate outerwear that combines well with the sportier elements of preppy style, and you’ll find no shortage of brands putting their own stamp on the garment.

Rugby shirt

A key piece in the preppy arsenal is the heavy cotton rugby shirt, with its requisite colour-blocked panels and contrast soft-rolled white collar. Great as a way to dress down some separates, the rugby shirt is the perfect mixture of collegiate sport style and casual off-duty comfort.

It’s a great way to inject some colour into your look, too, adding a bold dimension to a navy blazer and chinos or even a corduroy suit. Typically constructed from a heavyweight cotton, it’s a good year-round piece that offers myriad styling options.

OCBD (Oxford cloth button-down)

The OCBD is like the glue that holds the preppy look together. With a soft-rolled collar and even softer handle to the cloth, its charm is in the way it effortlessly dresses down tailoring and elevates knitwear.

The button-down collar is a throwback to the original polo shirt, which was devised by British army officers in India to prevent the collar flapping in their faces when they played polo.

Pastel tones are de rigeur in the summer months, nonchalantly worn with a French tuck into tailored shorts or chinos, the collar casually peeping out from a crewneck sweater. And when worn with a suit or tie, the OCBD softens the formality of what could otherwise be a stuffy, uniform look.

Straight-leg chinos

Menswear has a lot to thank the military uniforms of history for, not least chinos. Originally developed from cotton twill for British and French soldiers in the mid-19th century, chinos have become a preppy staple, with the influx of military khaki in the 50s further cementing their status in preppy menswear.

Cut with a straight leg and a reasonably low rise, the preppy style was and still is to wear chinos with a casual turn-up and loafers or boat shoes (more of which below). They are the perfect casual trouser being both lightweight and extremely versatile.

Give the salmon pink variety a swerve unless you want to be a feature of parody menswear websites and instead stick to the classic khaki, off-white and navy tones.

Corduroy

Once the preserve of geography teachers (forever society’s style whipping boys), corduroy has shaken off its fusty reputation to become a non-negotiable fabric in today’s discerning wardrobes. It’s not hard to see why – corduroy’s textural quality is second-to-none, with those vertical wales providing a great tactile finish.

Corduroy jackets and sports coats as well as two-piece suits slide straight into the preppy aesthetic with ease, pairing with an OCBD, crew-neck sweater or polo shirt for a relaxed tailored vibe.

Wider wales make more of a visual impact, while many brands are making shirts and trousers in a subtle micro-wale corduroy, too. Either way, it’s an excellent option for introducing a textural contrast into your preppy look.

Sports coat

While it might not get the heart racing, the classic sports coat is nevertheless an integral component of the preppy wardrobe. The style was originally created as a comfortable outer layer when participating in ‘sports’, namely plucking game birds from the sky.

As a piece of hunting kit, it was typically made from hard-wearing tweed and was cut in a relaxed, unstructured style to allow freedom of movement. Flannel, houndstooth and herringbone fabrics also became common in the sporting clubs of old, with many leaning on navy as a more cultured tone (bolstered by its nautical military heritage).

Regardless of whether you choose urbane navy or a more countrified finish, the silhouette is the all important feature. You want a softly tailored jacket with very little to no structure so that it drapes naturally. Navy works well contrasted with casual white trousers or chinos, while a brown houndstooth is well complemented with corduroy slacks or khaki pants.

Heritage fabrics

One of the main reasons why preppy style has enjoyed unrivalled longevity is that it borrows classic menswear fabrics from the past and reinterprets them in a way that feels modern. Heritage cloths such as tweed, herringbone and houndstooth, as well as patterns such as Madras check or Prince of Wales check, bring plenty of vintage sophistication to a look, but can be given a creative appeal when matched with contemporary loungewear or streetwear.

Think a tweed sports coat casually thrown over a grey hoodie or loopback crew-neck sweater and chinos. Or a bold Madras check shirt worn with a more understated charcoal flannel blazer. Heritage fabrics offer individuality and creativity while being far more versatile than you would think.

Leather loafers

While polished black oxfords were the preference of their fathers, the original 1950s frat boys preferred the more casual approach of the loafer, most notably G.H. Bass’ iconic Weejuns. Whether penny loafer or tassel, the classic leather slip-on is a must-have in your preppy shoe rotation, pairing nicely with the more tailored aspects of the look.

Today, you can be a bit edgier with your choice of loafer, opting for chunky soled varieties or fashion-forward styles with metalwork and embellishments. The once-lambasted white sock and loafer combo now seems to fly under the style radar, or you can opt to go sockless.

Either way, the loafer is a confidently stylish way to ground a seersucker suit or a pair of tailored shorts and an OCBD. Once again, it’s about complementing the polished leather of the loafers with a softer, more textural cloth in your outfit.

Nautical influences

Given that the Ivy League institutions are all dotted around the US east coast, it’s no surprise that the preppy aesthetic comes with a healthy sea spray of nautical references, as many images of preppy poster boy JFK on his boat will testify. The key pieces then are heritage knits, such as Aran and cable-knit sweaters, alongside more contemporary takes on the classic lightweight windbreaker.

The other great nautical item that fits perfectly with preppy style is the Breton top, that traditional long-sleeved cotton jersey with blue horizontal stripes. Easy to pair with a Harrington jacket or even a blazer, it adds a touch of Gallic maritime chic.

Finish the look with Sperry’s boat shoes, which are a must for preppy summer looks.

Seersucker

Seersucker was popular with Ivy League students in the 1920s and chief among them were Princeton’s preppy lot, who perhaps enjoyed the liberal connotations of that wrinkled, carefree finish. By the 1940s, Princeton’s boys’ predilection for seersucker had lent it something of a sartorial halo, so much so that the Duke of Windsor wore a two-piece seersucker while on holiday in the Italian Riviera.

Despite its slightly crumpled appearance, the suit was widely acknowledged as the pre-eminently tasteful summer fabric, sported by only the most discerning of stylish chaps. For a fabric whose roots were very much ingrained in the working class South, seersucker had, in a short space of time, become the choice of the rich and flamboyant (although that would again shift when jazz impresario Miles Davis wore seersucker on the cover of his live album At Newport 1958).

While it’s commonly found with a pinstripe, you’ll find many contemporary brands adopting it in block colours, trippier patterns and casualwear as well as suiting.

Shawl-collar cardigan

Texture and tactility is always important when putting a look together, preppy or not. It just so happens that traditional knits were and still are an integral part of preppy outerwear, in large part due to the nautical elements of the aesthetic. Hence the aforementioned Aran and cable-knit jumpers are a great way to get the look. One piece of knitwear, however, jumps to the front of the preppy queue: the shawl-collar cardigan.

Cardigans have that innately nerdy appeal, but the addition of the shawl collar brings a sophisticated formality to an otherwise relaxed garment. It’s still a very casual piece of knitwear, but the collar somehow elevates it. Steve McQueen was often seen wearing one unbuttoned with jeans and bashed up white sneakers and you’d do well to take your styling cues from the King of Cool.

Polo shirts

Polo shirts were preppy fodder long before Ralph Lauren decided to embroider a polo player on his horse on them, but credit where credit’s due – Mr Lauren eternalised the association and made the polo shirt preppy lore.

Can a man own enough polo shirts? Probably not. From cotton pique to knitted merino styles, the polo can take on both sporty casual vibes and high-end luxury. Easy to style, opt for classic white or pastel tones worn beneath a simple crew-neck sweater and finished off with a lightweight sports coat, chinos and loafers. As close as you’ll come to an Ivy League uniform.

Technical pieces

Harking back to the East Coast predilection for sailing style, more technical fabrics have infiltrated the modern preppy aesthetic in recent years, in the form of windbreaker jackets, technical blousons and gilets.

Aside from their obvious weatherproof functionality, these types of garments offer a nice textural contrast to natural fibres as well as juxtaposing the more tailored aspects of preppy style with a sporting, outdoorsy aesthetic.

A technical hooded jacket layered above an OCBD and merino sweater with straight-leg chinos and a pair of Sperrys is about as off-duty preppy as it gets.