How to Sport the Preppy Style Like a Pro

by Jamie

When looking at classic trends that have endured the test of time, preppy style undoubtedly sits comfortably somewhere near the top of the list. Here’s how to get the look!

Defined by smart crewneck sweaters, oxford button-down and polo shirts, chinos, navy blazers and refined accessories, the preppy look is about as unapologetically all-American as it gets. Here’s our essential guide to mastering the style like a pro, quicker than you shake a cufflink at.

Originally a look adopted solely by prep school students in North-eastern America, the preppy trend ultimately travelled far beyond the confines of college campuses, going on to shape the collections of many iconic designers such as Ralph Lauren.

While the trend’s popularity began to wane in the late 60’s/early 70’s, the 1980 release of Lisa Birnbach’s The Official Preppy Handbook – along with companies such as J. Crew stepping onto the scene – signified a renewed interest, and re-popularised the look for an entirely new generation. Initially intended as a satirical observation of upper and upper-middle class America, the guide instead became a coveted prep ‘how-to’. Covering everything from the appropriate sports to play to places to eat and what to wear, Birnbach translated the trend for those not in the know, and somehow achieved the impossible; she made ‘prep’ attainable.

How to Dress Preppy

Now I’m not going to lie to you, there is a science behind this trend. A preppy look for guys is simply not achievable if you want to just pick out elements of the look, as you won’t come across as authentic. Don’t worry though, as we are about to give you a head to toe breakdown on achieving the preppy look

The Preppy Shirts (and Collar Types)

The classic shirt is the Brooks Brothers button-down all-cotton oxford cloth shirt. Pink is the most famous colour…One should have the shirt also in yellow, blue and white – several in white…A couple of polo shirts in even, narrow horizontal stripes (red and navy, navy and white, yellow and white) are worth having.

– Lisa Birnbach, The Official Preppy Handbook (1980)

Closet Staples:

  • The Polo Shirt
  • The Oxford Shirt (often cloth and button-down) in a basket weave
  • The Seersucker Shirt

The Polo Shirt

The polo shirt is one of the most identifiable items in a preppy wardrobe, with labels such as Ralph Lauren and Lacoste making these signature pieces in their collections. The classic white is always a good choice, and looks great when paired with a navy blazer. Pastel shades fair well too. Just please do not pop your collars, as this takes away from any cool style you might have gained. Who said prep can’t be cool?

The Oxford Shirt

Much like the polo, the button-down oxford shirt is a key piece, and is often worn in a blue or candy stripe. Fun fact: Originally a sports shirt, its buttons were first used to stop the collar flapping up during tennis matches, proving style and practicality can indeed go hand in hand. Go for pastel shades such as pink for something a little more spring appropriate. While a more formal outfit will require a necktie (patterned choices work particularly well – think polka dots or stripes) going sans tie and throwing on a sweater will instantly transform it to a more casual look. Leaving the sweater out altogether works too.

The Seersucker Shirt

As well as regular cotton and cloth, seersucker shirts are also a prep must-have. Made from a puckered cotton material, its light and breathable nature makes it ideal for warmer weather. Perfect for those endless summers on daddy’s yacht, am I right? Go for this one in the classic pale blue and white stripe.

It is important to note that the shirt – whatever the style – is often tucked in for a more streamlined look when worn underneath a blazer.

The Collars

Choose those with button-down, plain point and rounded collars when selecting your shirts. The plain point is the collar of choice for the preppy gentleman, and its clean cut and classic shape make it one of the most versatile options. The club/rounded collar looks best when fastened with a collar pin and paired with a tie. Opt for a brightly coloured or striped necktie for true ‘Ivy League cool’.


The Preppy Sweater

Apart from being useful in keeping the body warm, sweaters are part of layering, often British, and make dandy accessories. Tie them around your waist, tie them around your neck…you can never have too many.

– Lisa Birnbach, The Official Preppy Handbook (1980)

Nothing says collegiate quite like a crew neck. The V-neck is also a viable (and more formal) choice. Both options look great when paired with a button-down oxford shirt and tie (without works too) as well as a polo shirt.  These two sweater styles are certainly going to be the main tools you want in your arsenal. The three key fabrics to consider are:

  • Cashmere
  • Wool/wool-blend
  • Cotton

As Birnbach suggests, tying a sweater around the neck or waist is encouraged, and helps to complete the look (while paying homage to the 80’s – rad!).

The argyle sweater can also (arguably) be classed as ‘preppy’. However, be sure to style these down with neutrals to avoid an unappealing clash of colours or *shudder* a tacky look.

The Preppy Blazer

A classic, navy blue blazer is my staple. It can take you from office meetings to dinner out with friends or family.

– Tommy Hilfiger, Designer

The navy blazer is synonymous with the preppy aesthetic, and its importance of tying the look together shouldn’t be underestimated. Opt for the single breasted blazer to truly encapsulate preppy style.  Solid navy is certainly the way to go if you’re aiming for a more traditional approach, and is perfect for achieving a smart, nautical feel that remains wearable. Choosing one with gold piping however, is ideal if you want to add a little something extra without straying too far from the style.

There are a variety of materials you can choose from, including poplin and wool (worsted wool being the most popular type due to its smooth and lightweight feel). An ill-fitting blazer can completely throw off a look. It is generally accepted that the correct fit is one in which the fabric hangs naturally from your body, rather than fitting snugly and restricting movement. Additionally, the shoulders of the blazer should have only slight padding.

While not necessarily a requirement, gold buttons work beautifully and undoubtedly add a touch of class as well as complimenting the navy well. Go for gold if you can. The last button must also always be left open (it’s a rule guys).

Ever versatile, the navy blazer can also be styled down with a plain, slim-fit tee. Keep the pocket square if you still want to retain a bit of old school sophistication.

The Preppy Tie

What a man wore…how his tie was tied…were of paramount importance.

– Jeffrey Banks and Doria De la Chapelle, Preppy: Cultivating Ivy Style, (2011)

Ties are a great place to start when injecting colour into your look, and are an ideal place to showcase your individuality. Go for repeated prints and bold primary colours.

The type of collar your chosen shirt has, will usually determine which kind of tie you will want to go for. For example, a small straight collar would require a thin tie while a wider collar requires a larger one.

The Preppy Chinos

…trousers are always flat front no matter what the fashion pundits tell you.

– J.P Gaul and Graham Marsh, The Ivy Look: Classic American Clothing – An Illustrated Pocket Guide Paperback, (2010)

Typically chinos are the trousers of choice, with a khaki shade being standard. The colour is both stylish and practical as it transitions easily from work to the weekend. However, don’t be afraid to experiment with bolder shades either.

As far as fit goes, they should always be tapered and straight-leg, finishing at the ankle and with the ends cuffed up. Oh and no pleats. Definitely no pleats.

The Preppy Footwear

When they’re checking to see if you’re prep, the first thing they look at is your shoes. From there they go to the rest of your wardrobe. The right shoes give you a fighting chance. The wrong shoes break you instantly.

– Lisa Birnbach, The Official Preppy Handbook, (1980)

So what are the right shoes?

Closet Staples:

  • Penny Loafers
  • Boat Shoe/Sperry Top-Sider

Loafers are often in leather, although experimenting with different materials can make for a welcome 21st Century update.

Socks are not at all a necessity (hello ankle cleavage). In fact, going sans socks is encouraged, particularly with boat shoes.

The Preppy Accessories

Closet Staples:

  • Leather belt
  • Cuff links
  • Scarf
  • Pocket square
  • Black/brown leather or brightly striped watchbands
  • A pair of tortoiseshell or Ray-Ban Wayfarer glasses
  • Monograms

For those that are a stickler for the rules, it’s essential that your shoes and belt match, especially when attending more formal events. Though the shades do not always have to match to a tee, they must at least be in the same spectrum.

While you can play around with many elements of the prep style, certain things are best when kept simple. Cufflinks are no exception. Plain gold or silver accents work well, and add just the right amount of low-key flair.

Scarves and pocket squares provide the prefect finish to an outfit, and show that you’ve put some thought behind your look. The options really are limitless when it comes to these, with neutral tones, bright hues and bold prints all being acceptable.

With watchbands, it’s quite literally all or nothing. For the minimalist, a plain brown or black leather band is ideal. If you fancy a bit more colour, then a striped band is the way to go. Navy, red, white, green and pink (yes, pink) all make for attractive colour combinations.

There are only really two choices of eyewear to consider when adding the finishing touches to a preppy get-up: classic round tortoiseshell and Ray-Bans. Relaxed preppy style indeed.

Monograms can also make for a nice embellishment to an outfit. That said, don’t be overzealous, and keep it understated if you do go this route. After all, wearing a large Yale crest on your blazer when you studied in Central London could make for awkward conversation at a dinner party.

Preppy Outfits for Guys: Experimenting with Textures, Colours and Patterns

While prep is built on the classics, there is always room for experimentation. Whether you simply want to introduce a bit of colour or go full-on eclectic, playing around with various textures, colours and prints will surely give any preppy outfit a fun and contemporary twist. Suede blazer? Why not. Velvet penny loafers? Yes please.

The choices are endless when it comes to fabrics, and it’s entirely up to you how far you’re willing to experiment. Corduroy, suede, linen, velvet – it’s all fair game.

Velvet is a great option, as it gives a cool edge while still exuding class, and looks particularly swish in the form of a pair of penny loafers or a well-fitted blazer. Luxe black, red and blue shades compliment velvet beautifully. Tweed is also something to consider, and provides a nice departure from a standard navy blazer while still remaining traditionally preppy.

Don’t be afraid to throw bright, bold colours into the mix. We’re talking bright blues, pastel pinks and greens to name a few. While striking colours may seem intimidating, it’s a great way to turn the trend on its head and ensure you don’t end up looking like one amongst many.

When it comes to mixing patterns, less is always more. A combination of two (certainly no more than 3) is ideal, and ensures that you don’t become a walking eyesore. Colours should remain in the same family, and prints look best when broken up with solid hues. A good example would be pairing a Fair Isle sweater in a neutral print with a plain coloured shirt in the same colour scheme. Patterns and colours look great on bow and neck ties as well, and are a good place to start for those who want to slowly introduce pattern and print play into their prep wardrobe.

The preppy look lends itself to layering, with a blazer over a crewneck sweater over an oxford shirt being standard. Why not go one step further and add a waistcoat for a refined yet eclectic feel? To really ramp up the retro, add in some brightly coloured suspenders underneath your blazer à la André 3000.

Prep in Popular Culture

Prep fashion has made its way onto both the small and big screen over the years, firmly cementing its place in popular culture. For those seeking further inspiration, we’ve compiled a list of three must-see films that define what it is to be a true prepster.

  1. American Psycho – Gruesome subject matter aside, this infamous flick set against the backdrop of a 1980’s Wall Street is prep overkill (pun intended). Christian Bale’s Patrick Bateman and his fellow Manhattanites are rarely seen without their tortoiseshell glasses – Oliver Peoples to be exact – brightly decorated ties and tailored pinstripe suits.
  2. Wolf Of Wall Street – Also set in the 80’s, this film has polo shirts, Ray-Bans, and crew neck sweaters in abundance (Jonah Hill’s character appears to favour the sweater around the neck approach.) There’s also a ridiculously lavish party on a yacht midway through the film. It doesn’t get much preppier than that.
  3. Dead Poets Society – This Robin Williams helmed drama is a true lesson in East-coast prep. Main characters that attend an Academy? – check. Enough loafers and navy blazers to make even the ‘Iviest’ Leaguer proud? – check. File this one under ‘prep classics.’

Famous Preppy Guys

Still stuck for ideas on preppy looks for guys? Take a style note from these famous faces on how to dress preppy effortlessly:

  • André 3000 – Whether rocking suspenders, three-piece suits, sports coats or bow ties, the rapper isn’t afraid to mix colours and prints together achieving a retro yet perfectly groomed feel. Look to him for inspiration if you like your prep with a touch of outlandish cool.
  • Paul Newman – The epitome of a true gentleman, Newman looked equally at home in a V-neck as he did in a polo shirt.
  • Steve McQueen – The ‘King of Cool’ rocked a pair of khakis better than most.
  • John F. Kennedy – A Harvard alum, it comes as no surprise that the former Leader of the Free World had the style down to a science. Ray-Bans and polo shirts were his ‘off-duty’ pieces. Talk about having the presidential seal of approval.
  • Johannes Huebl – Navy blazers, crewnecks and oxford button-downs are all in a day’s work for fashion it-girl Olivia Palermo’s equally stylish other half.
  • Eddie Redmayne – The actor and former Burberry model nails the chino, sweater and button-down combo every time.
  • Kanye West – The controversial rapper is always breaking the boundaries of both music and fashion, and his approach to prep is no different.

Preppy Men on the Street

Now we have looked at all the famous nods towards preppy, let’s see how men are styling the preppy look on the streets. One of the key things to consider when incorporating prep into your look, is colours. Unless you are going for a formal feel, then a pop of pastel really helps to hammer in the trend.

Notable Preppy Labels

The following labels are all known for their preppy style, so look to these for some sartorial guidance:

  1. L.L. Bean – Founded in the early 1900’s, the clothing and outdoor equipment retailer had a significant influence on prep culture.
  2. Brooks Brothers – Still a favourite with Ivy League Universities, Brooks Brothers was another of the originals.
  3. Tommy Hilfiger – Hilfiger released a perfume named Eau de Prep in 2011. That pretty much says it all. Heavily influenced by the New England style, kitting yourself in his clobber will have you feeling – and looking – a million bucks.
  4. Ralph Lauren – Going strong since the late 1960’s, no one does classic prep quite like Ralph Lauren.
  5. Barbour – Simply put, a one stop shop for all your preppy outerwear needs.
  6. J. Crew – Simple, classic and comfortable, J. Crew is a prep favourite.
  7. Burberry – Synonymous with the ‘British Gent’, Burberry is a must for clean, smart style.
  8. You Must Create (YMC) – Shunning the latest trends in favour of functionality, this brand aims to make ‘intelligent clothing that is wearable.’ Check them out if you’re aiming for understated cool.

Your Quick Guide to Nailing Preppy Fashion

  1. Remember the three C’s: collegiate, clean and cuts. In other words, the look must be rooted in the collegiate style, have a neat and clean finish and be cut well (specifically the blazer).
  2. Oxford/polo shirts, a good quality sweater, a navy blazer, chinos and boat shoes are your essentials.
  3. Always leave the last button on your blazer open. Always.
  4. Be bold with your colour choices. Don’t be afraid to experiment with colour and texture for a more modern look.
  5. Never compromise on quality. It shows. By no means does the outfit have to cost a fortune, but it certainly shouldn’t look cheap either.
  6. Ties work equally well in brighter colours or when patterned. Swap a necktie for a bow tie once in a while too.
  7. Button-down, plain-point and rounded are the three main collars. Choose your tie accordingly.

A Brief History of Preppy Style

Also referred to as the ‘Ivy League Look’ – as it wasn’t uncommon to see the style among students at esteemed Ivy-League institutions such as Harvard, Yale or Princeton – preppy fashion emerged in the early 1900’s, hitting its stride mid-century. Labels such as Brooks Brothers and J. Press were instrumental in this, with some of their stores actually being located on these campuses.

The term ‘prep’ takes its name from the private preparatory school that students hailing from wealthy families would attend before college. These were highly-regarded, and those who attended one frequently went on to study at a prestigious Ivy League University afterwards. Nowadays though, successfully achieving the preppy look usually lies more in the quality/cut/style of the clothing itself rather than your background or social standing. Spiffing news for any guys out there who don’t vacation at Martha’s Vineyard or know anyone affectionately nicknamed ‘Muffy’.

On That Note…

While there is technically a right and wrong way to do prep, there is certainly nothing wrong with adding your own twist and making the trend unique to you. Style is about individuality after all. The most important thing to remember however, is that at its essence, the preppy style is defined not just by the clothes but the attitude that goes along with it. So gentlemen, by all means dress well, but don’t forget to carry yourself well too.

Feature image from Pinterest

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