At first glance preppy may seem like a fashion disaster. After all, few style clans can team washed-out red trousers with a green polo shirt, mix pink with purple, yellow with honeydew, set a bold stripe next to a Madras plaid, and live to tell the tale. Even fewer would actually want to.

This was the preppy of Lisa Birnbach’s defining and cheekily undercutting ‘Official Preppy Handbook’, 1980’s seminal homage to the life of Anglophile East Coast gentrification – the monied, relaxed and subtly style-aware existence of messing about on the Hamptons’ tennis and croquet courts, with horses, yachts and clubs (both golf and country), bow-haired girl in the one hand, G&T firmly in the other. Preppy is a label that has stuck. Florida’s Koch Crime Institute once identified a criminal youth clan – comprising upper middle-class, high-income, socially-active members – as ‘preppy gangs’.

But there is more to the preppy uniform than a love of colour mixing. Its 1980s incarnation was the style of discreet wealth for young American East Coasters, though preppy became established as benchmark in menswear through US pop culture. More positively, Hollywood late 1970s/early 1980s ‘frat pack’ movies such as ‘Animal House’, ‘The Sure Thing’ and ‘St Elmo’s Fire’ saw white-toothed and casually thrown together Rob Lowe clones – who looked rather good for it. Music had preppy dabbler Michael Jackson, all white socks and loafers, as well as the Beastie Boys and any number of upscale B-Boy skate bands to look to – their version was more one of an appropriation of the rich man’s playthings as social commentary, undermining the symbols of wealth with irony and faux club crests, but it has also given the look longevity.

GANT Rugger preppy clothing campaign image
Modern day preppy from GANT Rugger

Yes, Birnbach appreciated that preppy had its limitations: loaded with connotations of class and wealth, and even too restricted by age limits. Forty was, she determined, the age when you could finally wear your polo shirt collar turned down. Additionally, here men face an additional problem: preppy may speak style in the US language of cool, but in the UK it says ‘sloane’ – to anyone beyond Chelsea the sartorial kiss of death. So, to be sure, you have to look further back to get it safely right. And, certainly, preppy goes back much further than many are aware – such that it allowed US designers the likes of Tommy Hilfiger and Ralph Lauren to build empires around it.

This is the preppy of the 1950s and 1960s – the preppy that brought together ex-US forces khakis and Brooks Brothers or Gant Oxford shirts, saddle shoes and sweatshirts, Bass Weejun loafers and regimental ties, shawl-collar cardigans, hopsack blazers and slimline European suits, worn white pumps and plain white T-shirts. This is the preppy that then put together what in isolation can seem rather pedestrian clothing – the clothes of an older generation even – in such a way as to look just… right. This is the preppy that inspired the Italians that then inspired the mods, that lent elements of its dress sense to ska and skinhead.

Paul Newman in a preppy all-white outfit
Paul Newman

Indeed, this is the preppy that’s arguably the single most influential look in 20th century menswear, born of the attire of the US’s elite Ivy League students and their demand for practical, hard-wearing but always at least elegant attire (the definition of smart casual). This is the preppy of Paul Newman, JFK and Miles Davis. Wear preppy and, while you may not be the height of fashion, you cannot go wrong.

“Prep is rooted is all about confidence, eclectic details and not taking yourself too seriously. Prep can be classic, laid-back, or even rock ‘n’ roll. But it always works.” – Tommy Hilfiger

Miles Davis - Seersucker
Miles Davis wearing Seersucker

Davis was a case in point. Contrary to his culture and his race – preppy was originally both very monied and very white – Davis was a regular of Charlie Davidson’s The Andover Shop in Cambridge, Massachusetts, the store where Ivy League style took hold. Miles’ preppy was a look that helped define ‘jazz cool’, but also helped win what was then still an avant garde form of music a new acceptability.

But ‘The Warlord of the Weejuns’, as critic George Frazier would dub Davis on the liner notes for a greatest hits collection in 1965, proved too that you could wear preppy in your own way. Davis would wear drop-shoulder seersucker sports jackets – they were easier to play trumpet in – without cuff-buttons or breast pocket, or formal, double-breasted suits with more casual patch pockets; a knotted neckerchief under the button-down collar of his shirts, often with an unusual pullover placket.

JFK was a huge preppy clothing proponent
KN-C23203. President John F. Kennedy and Peter Lawford Aboard the Yacht “Manitou” – 12 August 1962. Credit: Robert Knudsen. White House Photographs. John F. Kennedy Presidential Library and Museum, Boston

Yet might Kennedy have even owed his presidency to preppy? It’s been suggested at least that the way this Ivy-Leaguer dressed was in part what helped set him apart from previous generations of dowdy politicians, that made him strike the populace as youthful and dynamic. Such was to become JFK’s influence that British boys of the time were said to have requested their hair styled into Kennedy’s trademark tousled thatch, carefully contrived to look unruly – a touch of artful dishevelment being part of the preppy code.

One desperate hat-maker wrote to Kennedy pleading to him to wear a hat – JFK had a notorious dislike of hat-wearing: “You have set a new pattern for youth,” he told Kennedy. “What may be a personal attitude for you is becoming a must for these young hatless people…” The popularity of button-down shirts and dark suits all changed according to Kennedy’s unofficial endorsement. Arguably preppy has never lost the agelessness that Kennedy gave it.

Indeed, his – as was the case for the first wave of preppy – was essentially a minimalistic, classic style. Certainly it was a long, long way from the second wave of the 1980s, with its love of excessive, look-at-me colour and pattern. Really, it’s a shame the two have ever been confused. One trusts that, after reading this, the reader feels somewhat put straight. And is ready to look to an aesthetic more than half a century old for some lifelong style tips.

The Best Preppy Clothing Brands For Men

Ready to introduce some American Prep into your wardrobe? Look no further than Ape’s rundown of the very best preppy brands on the planet…

Brooks Brothers

Non-Iron Regent Fit Oxford Sport Shirt, £115 at BROOKS BROTHERS >
Cable-Knit Crewneck Cashmere Sweater, £395 at BROOKS BROTHERS >

No one can deny Brooks Brothers is an American icon. Founded in 1818 in New York by Henry Sands Brooks, it introduced its first read-made suits way back in 1849. To give this come context, 1818 was the year the White House officially reopened after being burned in 1814 by the British in the War of 1812. Brooks Brothers have provided preppy clothing for the American elite (and beyond) ever since. Favoured at the highest level by many a US president, including most famously JFK, the brand is noted for its high-quality, timeless clothing. A true American institution.

J.Crew

Garment-Dyed Stretch-Cotton Poplin Shirt, £65 at MR PORTER >
484 Slim-Fit Pant In Stretch Chambray, £75 at J.CREW >

American brand J.Crew was founded in 1947 by Mitchell Cinader and Saul Charles and today operates around 450 stores in the US. Its focus is style over fashion, but with a distinctive preppy edge. In it’s campaign and lookbook shots you’ll find modern pairings of sneakers with suits and brogues with jeans, alongside traditional colour-blocking and pattern mixing. The quality is good, and the price point reasonable.

Ralph Lauren

Logo-Embroidered Single-Cuff Cotton Shirt, £85 at MATCHESFASHION >
Slim-Fit Polo Shirt, £79 at END CLOTHING >

American designer Ralph Lauren (born Ralph Lifshitz) founded the Polo Ralph Lauren Corporation in 1967. It was 1977, 10 years after the company was founded, when it introduced the signature cotton mesh Polo shirt in various colours. Featuring the now-iconic polo player logo on the chest, the shirt became emblematic of the preppy look, and put Ralph Lauren on the map. Lauren himself breathed the American Dream into a clothing (and more) brand – creating the embodiment of a particular lifestyle or way of life.

Drake’s

Drake’s Beige Brushed Cotton Twill Chino, £285 at DRAKE’S >
Drake’s Pale Blue Oxford Regular Fit Shirt with Button Down Collar, £135 at DRAKE’S >

Founded by Michael Drake in 1977 in London’s East End, Drake’s quickly earned a reputation for producing quality scarves and shawls for high-end fashion boutiques and traditional tailoring houses. This initial success saw the company branch out into ties and pocket squares for which the brand is recognised for. A philosophy of producing timeless pieces that have a relaxed elegance, to exacting standards ran through the Michael and the brands’ veins. A recipe for success in itself, soon picked up on by the style and tastemakers in the UK but never by the mainstream – intentionally no doubt.

Jack Wills

Marlow Cable Crew Neck Jumper, £69.95 at JACK WILLS >
Tamar Stretch Skinny Chinos, £57.95 at JACK WILLS >

Jack Wills was founded by Peter Williams and Robert Shaw in 1999. The brand’s original store opened at 22 Fore Street, Salcombe and was created to, “bottle what being at a British university was all about”. Today the brand combines British heritage style with a youthful, irreverent and carefree edge. The brand went mainstream in the 2000s and was viewed as Britain’s answer to Abercrombie & Fitch.

Abercrombie & Fitch

Pop Icon Crew Neck T-Shirt, £17.99 at ABERCROMBIE >
Icon Zip Through Hoody, £72 at ABERCROMBIE >

With a long and rich heritage, Abercrombie & Fitch was founded in 1892 in New York, by David T. Abercrombie and Ezra Fitch, making its name as an elite outfitter of sporting and outdoor goods. Today it’s known for its racy marketing photography with semi-nude males and females, often employees of its stores. It’s well-known moose logo was once the ‘badge’ to be seen in, but its pull has since waned. However, with a change in tack in recent years the brand has refocused on what helped made its name in the fist place: high-quality preppy basics that epitomise that laid-back California lifestyle.

Tommy Hilfiger

Engineered Oxford Shirt, £85 at HOUSE OF FRASER >
Brooklyn Regular Fit Shorts With Belt, £70 at HOUSE OF FRASER >

Founded by Thomas Jacob “Tommy” Hilfiger in 1985, the brand is known for its classic Americana style with a preppy twist. Hilfiger is still the brand’s principal designer despite having sold the company back in 2006 for $1.6bn. While the label has suffered in recent years, since 2017 it has seen somewhat of a revival of fortunes thanks to the revival of 1990s menswear.

Kent & Curwen

Appliquéd Striped Cotton Polo Shirt, £135 at MR PORTER >
Rose Emboridered Hoop Striped T-Shirt, £65 at KENT & CURWEN >

Led by Daniel Kearns as Creative Director, British heritage brand Kent & Curwen has almost become synonymous with ex-footballer and company investor David Beckham. The duo are involved in all aspects of the business, including product development, market expansion, advertising and store design and location. Expect to find bold logos, Ivy League-inspired rugby shirts and solidly-made basics.

Gant

Slim Fit Oxford Shirt, £85 at GANT >
Tennis V-Neck Sweater, £150 at GANT >

GANT was founded in 1949 by Bernard Gantmacher as a shirtmaking company in the college town of New Haven, Connecticut. It quickly became known for its Oxford shirts, which featured the perfect collar roll, a locker loop, box pleat, back collar button and button tab. Located near to Yale University, GANT played a major role in shaping the Ivy League Look as we know it today. We must also mention the brands GANT Rugger line, sub-line with a heightened level of cool.

Hackett

Stripe Polo Shirt, £95 at JOHN LEWIS >
Blue Blazer, £350 at JOHN LEWIS >

Despite humble beginnings, Hackett was founded in 1979 by Jeremy Hackett and Ashley Lloyd-Jennings from a stall on London’s Portobello Road selling used clothes. Hackett has gone on to become a stalwart of the new breed of fine British brands. Today, you’ll find a wide-spanning range that runs the gamut from high-quality basics right through to bespoke tailoring.

G.H.Bass

Weejuns Larson Penny Loafers Black Leather, £135 at G.H. BASS >
Weejuns Larkin Tassel Loafers Wine Leather, £135 at G.H. BASS >

G.H. Bass & Co. dates back to Maine in 1876 when the footwear company was founded by George Henry Bass. But it wasn’t until 1936 – when G.H. Bass put a stylish spin on a Norwegian farm shoe designed for “loafing in the field,” dubbing them “Weejuns” – that the brand went mainstream and history was made. Known as the world’s first penny loafer, the company have never looked back. Arguably the defining preppy shoe, the iconic Weejun has been a firm favourite of everyone from Ivy Leaguers to the late Michael Jackson ever since.

Sperry

Topsider Authentic Original 2-Eye, £89 at END CLOTHING >
Authentic Original Leather Boat Shoes, £85 at MR PORTER >

Sperry is the original American brand of boat shoe, first designed in 1935 by Paul A. Sperry. Rumour has it that while sailing on the Long Island Sound, Sperry slipped on the deck of his boat and fell overboard – an experience which drove him to develop a safer, non-slip shoe. Multipurpose, the Sperry Top-Sider Deck (or boat) shoe has been seen on a variety of celebrities and presidents including, again, JFK.

Honorable Mentions

Honourable mentions should go to the likes of Billy Reid, Barbour, Lacoste, Bonobos, L.L. Bean, Crew Clothing, Pendleton, Perry Ellis, Vineyard Vines, Kiel James Patrick and Armor Lux – all quality brands which fit the preppy bill in parts and narrowly missed out on this list.