Stumped by the eternal mystery of smart-casual dress codes (who isn’t)? You might want to enrol in preppy style for a semester or two. Okay, it’s synonymous as the Sloaney Pony uniform of choice but now fashion has rightly reclaimed preppy as a nonchalant way to do smart-casual in the 21st century. And there’s not a red chino in sight…

Preppy style evolved from quintessentially Ivy League origins, first sported by America’s East Coast elite in the early 1900s. More formal than the preppy looks we often see today, it became a way of dress for students attending prestigious universities like Harvard, Yale and Princeton.

The preppy aesthetic reached its mainstream heyday in the late 1950s – adopted (with a twist) by Hollywood hipsters like Steve McQueen and Paul Newman, collegiate style suddenly became iconic off-duty clothing that anybody could wear.

“Today, preppy is a look referenced and modernised as classic American style,” says Olie Arnold, style director at Mr Porter. “For me, preppy style can simply be tailored basics with hints of colour to add a bit of flair to your outfit. A great way to interpret it now is with a varsity jacket, combined with chinos and a pair of loafers.”

For a masterclass in modern preppy style, look to the likes of David Gandy, out-there André 3000, and Eddie Redmayne when the tux is at the dry cleaners. Here’s how to do preppy, well (Ivy League major not essential).

The Rules Of Preppy Style

Whether you’re a fashion freshman or senior prep pro, follow these styling pointers to look more modern-day JFK, less Made in Chelsea reject…

Collar Etiquette

No poppin’ here, thanks. Keep it down.

Try One Statement

Never, ever several – unless you are actually André 3000. “Build the preppy look around a staple piece, like a varsity jacket or madras check shirt,” says Arnold. “This is always easier if you keep your outfit’s colour palette to a minimum.”

How to wear men's preppy clothing in a modern way

unknowntommy hilfigerCCCgant

Stay On Neutral Ground

“Don’t overcomplicate the look with bright collegiate colours. Stick to neutrals if you want a more grown-up version of preppy,” says Carl Thompson, men’s lifestyle blogger and founder of hawkinsandshepherd.com. “For foolproof preppy, try contrasting a navy sweater or blazer with light chinos.”

Keep It Classic

Vintage shots of 1960s Ivy Leaguers still don’t look out of place now. Why so? “Sticking to classic preppy pieces like a cotton cable jumper will make the trend look timeless,” advises Gant’s design team. No Instagram archiving over here.

Classic men's preppy outfits and style

brooks brotherstommy hilfigerBonobosMassimo Dutti

Clean Cuts

“The preppy look is clean and polished so make sure each piece fits perfectly and tuck in any loose ends or unfinished edges,” says Emma Burke, fashion editor at Jules B. Final touches like monogram embellishment on shirts and sweaters will also elevate your prep credentials.

Use Unexpected Colours

If you want to venture into more colourful, traditional preppy ground, keep it quirky. Patrick Grant, designer of Hammond & Co. at Debenhams as well as his own label, E. Tautz, says, “Start off with a base of classic tailoring, like tweed and flannels, and layer on top bursts of colour in your shirts, knits and socks – think lemon, peach or mint green for ultimate old-school preppiness.”

Bold coloured preppy outfits for men

tommy hilfigertommy hilfigerralph laurentommy hilfiger

What Not To Wear

Red. Trousers. Ever. The. End.

10 Preppy Pieces You Need In Your Wardrobe

Oxford Shirt

Formal shirts aren’t going to cut it for prepping up, so button up its off-duty little brother instead. Less structured a cut from a slightly thicker material, Oxford shirts nail that tricky smart-but-not-stiff vibe.

Thompson says: “Still considered a sports shirt, a decent button-down is the ultimate staple for prep style. Wear it under a navy blazer or varsity jacket.”

Key Brands: J.Crew, Ralph Lauren, Gap, Gant, Brooks Brothers, Club Monaco, Uniqlo

The Best Preppy Oxford Shirts For Men

POLO RALPH LAUREN Logo cotton-oxford shirt - click to buyJ.CREW Slim-Fit Button-Down Collar Oxford Shirt - click to buybrooks brothers Solid Oxford Sport Shirt - click to buygap Oxford Shirt - click to buy

Navy Blazer

Half nautical, half head boy, a navy blazer is the signature, cornerstone piece of preppy-ville. “Always wear your shirts tucked in when you team with a blazer,” says Burke. “This is all about creating that Ivy League vibe, so don’t compromise on quality – picking the right jacket in the right fabric and fit is key to setting off a well-rounded, collegiate look.”

Feeling brave? Experiment with lighter pastel tones if you prefer a more dandyish vibe for a summer wedding.

Key Brands: Brooks Brothers, J.Crew, Tommy Hilfiger Tailored, Hackett, Crew Clothing, Charles Tyrwhitt

The Best Preppy Blazers and Sports Coats For Men

j.crew Unstructured Ludlow blazer - click to buyTOMMY HILFIGER MEN'S CLASSIC BLAZER - click to buyralph lauren Polo Doeskin Blazer - click to buyCT Slim fit light blue Italian wool blazer - click to buy

Cable Sweater

Warning: only nonchalantly drape over shoulders if you live within a 0.5 mile radius of Chelsea’s Kings Road and want to risk being mistaken for Spencer Matthews. Otherwise, the cotton cable knit jumper is the dependable piece that can be worn day or night, and dressed-up or down.

Gant’s design team suggests formalising it with a button-down shirt and blazer, or keeping it casual with a pair of chinos.

Key Brands: Kent & Curwen, Gant, Jack Wills, Ralph Lauren, Gap, Abercrombie & Fitch, Barbour, Tommy Hilfiger

The Best Cotton Cable Knit Sweaters For Men

GANT Cotton Cable Crewneck Jumper - click to buyjack wills MARLOW CABLE CREW NECK JUMPER - click to buygap Cable-Knit Pullover Crewneck Sweater - click to buyabercrombie ICON CABLE KNIT SWEATER - click to buy

Varsity Jacket

One key piece can make or break your preppy vibe – and if you’re not a blazer kinda type, the varsity jacket is an instant outfit transformer. Nobody pulls off a red, appliqued varsity better than noughties Kanye, but for less OTT options stick to black or deep navy that go with (almost) anything.

Prioritise premium fabrications and a pared-back palette for an investment piece that works in all seasons. Think of it as preppy’s alternative to a leather jacket.

Key Brands: Golden Bear, J.Crew, Ralph Lauren, Coach, Opening Ceremony, Todd Synder, Gucci, Club Monaco

The Best Varsity Jackets For Men

Wallace & Barnes cotton varsity jacket - click to buyGOLDEN BEAR Virgin Wool-Blend And Leather Bomber Jacket - click to buyCLUB MONACO Wool-Blend Twill And Leather Bomber Jacket - click to buycoach Varsity Jacket - click to buy

Rugby Jersey

You don’t have to be a posh jock called Rory to pull off preppy sportswear. Even if you’ve never chased an egg, you can give the illusion you might* in a rugby jersey (*this sweater will probably/definitely never see a speck of mud). Use it as a layering piece over a shirt, or throw it on under a jacket to inject some colour/stripes/both into your outfit.

Ralph Lauren’s iconic long-sleeved rugby shirt is hard to beat when it comes to pulling off the Ivy League team captain look convincingly, and it comes complete with a crisp white collar. Just add blazer.

Key Brands: Ralph Lauren, Canterbury, Kent & Curwen, Hackett, American Eagle, Jack Wills, Howick, Crew Clothing

The Best Preppy Rugby Shirts For Men

ralph lauren The Iconic Rugby Shirt - click to buyKENT & CURWEN STOKES 3 LIONS K.C. ICONIC RUGBY - click to buyAE RUGBY POLO - click to buyCREW LONG SLEEVE RUGBY SHIRT - click to buy

Chinos

Put red trousers on the Banned For Life list. For effortless prep pants with repeat wear potential, chinos in an earthy tone is where it’s at. Think of them as a smarter take on jeans that won’t piss off your boss.

“Go for a relaxed but tailored fit – too much of a slim fit just feels outdated,” says Pelle Lundquist, creative director and co-founder of new Scandinavian brand A Day’s March. “Style them with an Oxford shirt, or even T-shirts and hoodies for a cool spin on preppy.”

In summer, give your ankles some DIY air con by loosely rolling up chino hems for a more relaxed crop.

Key Brands: Gap, Banana Republic, J.Crew, Gant, Club Monaco, Incotex, Uniqlo

The Best Preppy Chinos For Men

gap Vintage Wash Chinos - click to buyGANT Summer Chinos - click to buyj.crew 770 Straight-fit stretch chino - click to buyBR Mason Tapered Rapid Movement Chino - click to buy

Loafers

Getting your footwear right can take your look from college dropout to Ivy League. “You can’t go wrong with a black leather penny loafer from John Lobb or brown suede loafer from Edward Green,” says Arnold. For extra detail, loafers are the one piece where guys can legitimately wear tassels and not get crucified at the bar.

If you want to go less formal, look for rubber-soled boat shoes – best reserved for spring/summer, because nobody enjoys soggy nubuck.

Key Brands: G.H. Bass, John Lobb, Edward Green, Sebago, Sperry Topsider, Gucci, Cheaney, Brooks Brothers, Church’s

The Best Preppy Loafers For Men

EDWARD GREEN Portland Leather-Trimmed Suede Tasselled Loafers - click to buyWEEJUNS LARSON MOC PENNY NAVY LEATHER - click to buygucci 1953 Horsebit leather loafer - click to buySPERRY TOPSIDER AUTHENTIC ORIGINAL 2-EYE - click to buy

Seersucker

Ditch the tweeds for summer and switch to breathable seersucker tailoring. It’s far less structured than most suiting, so get the fit just right to avoid weird bunching and wrinkling that will throw the look off.

“Learn to love a clash – try a seersucker blazer with a colour stripe Oxford shirt and club tie,” says Grant. “If it looks slightly wrong, you’ll know it’s right.”

Key Brands: Brooks Brothers, Thom Browne, Hackett, J.Crew, Club Monaco, Jack Wills, Todd Synder, Howick

The Best Seersucker Tailoring For Men

topman Navy Seersucker Smart Blazer - click to buyHOWICK Hamden Seersucker Blazer - click to buyTHOM BROWNE Single-breasted striped cotton-seersucker suit - click to buytodd snyder SUTTON SUIT PANT IN ITALIAN SEERSUCKER - click to buy

Polo Shirt

When layering isn’t an option in summer, a low-key polo shirt will keep you looking more preppy, less sweaty. Think Fred Perry’s classic contrast-collar polo shirt tucked into chino shorts.

“For me, the epitome of preppy is being casually cool with pieces like sports-style polo shirts,” says Declyn Cooper, menswear buyer for Slaters. “It’s an easy way to incorporate a preppy twist on an outfit that still represents your own individual style – just keep your collar down.”

Key Brands: Fred Perry, Lacoste, Ralph Lauren, Original Penguin, Hackett, Abercrombie & Fitch, Tommy Hilfiger

The Best Polo Shirts For Men

FRED PERRY TWIN TIPPED POLO - click to buyoriginal penguin THE EARL CHAMPIONSHIP POLO - click to buyLACOSTE Cotton-Piqué Polo Shirt - click to buyPOLO RALPH LAUREN SLIM FIT POLO - click to buy

Accessories

When it comes to trends, over-accessorising can be outfit self-sabotage. Preppy may be polished but you only need two or three extras – max – to pull your outfit together.

“A preppy outfit isn’t complete without sharp accessories, so make sure your belt matches your shoes and add a Daniel Wellington-style watch to finish the look,” suggests Tony Field, managing director of Fields Menswear.

Go for collegiate stripes on your tie at formal events and woven leather around your wrist or waist when things are more casual.

“Don’t forget that the preppy look doesn’t stop with your outfit: slick grooming and attention to detail is a must in this trend,” says Field.

The best men's preppy accessories

charles tyrwhitt traditional stripe classic tie - click to buyDANIEL WELLINGTON MEN'S GLASGOW 40MM WATCH - click to buyMIANSAI SILVER HOOK ROPE BRACELET - click to buyJ.CREW 3cm Brown Woven Leather Belt - click to buy