Preppy Aesthetic: How to Get the Ivy League Look (2024)

What is a preppy aesthetic?

The preppy aesthetic, characterised by crisp plaid button-downs, chino shorts, loafers and brightly colored polos with popped collars, has been making waves in style circles lately as the look has seeped into many new brands, including retailers such as Urban Outfitters and J. Crew.

In fact, the term preppy was even added to the Oxford English Dictionary in 2007. So how do you get this very specific look that has become synonymous with Ivy League fashion? It all starts with picking your clothes wisely and shopping smartly.

What is the style preppy?

The preppy aesthetic has derived from an American subculture formed around old private college preparatory schools. The style was originally based around the school's uniforms but has since then grown and evolved into becoming a genre all of its own.

With its foundation in wealthy American middle and upper classes the dress is generally quite conservative. Yet still distinctive enough to be identifiable as an affluent young member of this elite club.

Who created the preppy aesthetic?

The preppy look is very similar to Ivy League and shares a lot of similarities in terms of conservative dress. Ivy League of course being born out of Ivy League Universities such as: Harvard, Princeton, Columbia and Yale. It originated in 1912 but had well and truly gained pace by the 1950s as a subculture worth associating with.

Here in the UK the style is very similar to the casual dress of wealthy aristocracy or upper classes. Mainly inspired by the sports commonly played such as: sailing, polo, hunting, rowing, golf, tennis and rugby.

Generally the style sees a merging of sports clothes with more traditional garments such as tweed sports coats and brogues. This keeps the youthful vibrant aesthetic, which contrasts from maybe the more formal attire of their older generation.

Similar to the USA it is a style associated with the most prestigious Universities such as: Oxford and Cambridge. With the children of wealthy upper class families who previously attended private fee paying schools then proceeding to University.

The original brands J. Press and Brooks Brothers, who catered for the 'prep aesthetic', interestingly both opened stores on the campuses of the top Ivy League schools. A certain strategic move which no doubt paid dividends; as it cemented them as the go-to brand to get the latest look.

The style very much moved into the mainstream by the 80's. Popularised by brands such as Ralph Lauren and of course it's aptly named spin-off brand Polo. Which makes no bones about its target market considering it features a polo played as their logo.

The style is still very much popular in America and as mentioned above it has been imported into UK Universities. With many young upper class parents sending their children to these prestigious Universities.

Which of course are based in cities rich with history and classic architecture. Which allows students access not only to their uni but also surrounding locales which they can then socialise at further reinforcing the stereotype and increasing it's popularity.

Princess Diana - The Queen of the Preppy look

Princess Diana was the queen of the preppy look in the 1990s. She popularised the classic blazer-and-jeans combo, and was often seen in button-down shirts and turtlenecks. Diana's preppy style was both polished and relaxed, and it's something that you can easily recreate for yourself.

To get the Diana-inspired preppy look, start with a few key pieces like a blazer, jeans, and a button-down shirt. Then add in some classic preppy accessories like pearls, loafers, and a scarf. With these essential pieces, you'll be able to create endless chic and stylish looks that are perfect for any occasion.

Even her casual sports attire looked elegant, combining bold graphic sweaters, shorts and sports socks.

Pairing a Varsity jacket over an otherwise more conservative all black outfit really gives it a preppy lift.

How can I look more preppy?

The Layered Look

Characterised by its iconic use of layering up casual sports items such as rugby shirts with more traditional items like tweed sports jackets and school blazers makes this look so instantly recognisable.

Dressing in layers will not only make you warm, but also gives you the opportunity to dress according to your surroundings, keeping you comfortable no matter what time of year it is.

The best way to build a preppy outfit? Start from the bottom! Picking out an appropriate shoe or pair of boots is essential, after all they're going to be touching (and holding) your feet for hours on end.

For example I'm rocking my navy suede penny loafers today, but I could have worn sneakers if I was just planning on running errands in town or wellies if we were heading out into the countryside.

An iconic pairing synonymous with the preppy look has to be the brogue paired with the traditional American style sports sock. Something which would have previously been seen as a sin. Wearing anything other than a dark complimentary sock with a more formal shoe like a brogue highlights the playful, youthful nature of this style.

When it comes your bottom half it used to be more of a slim fit chino generally. However, now more recently the preppy thing to wear the oversized, high waisted, high rise trouser; usually found hovering above the loafer below. Both men and women have been rocking this look for the past few seasons and we think it's a style that's here to stay.

As found with all preppy style ladies, skirts are also generally quite conservative, never too short. Pleated is a common style, made from tweeds or plaids harking back to the traditional roots of this look. Inspired by the uniforms of private, fee paying schools, they're commonly paired with blazers or sweaters.

Ivy league style t-shirts are often polo styled, long sleeved and white striped - always coupled with a blue blazer for a uniformed feel. From there it's about accessorising appropriately. Maybe adding some shades to add an air of sophistication or even wearing something underneath - depending on how much coverage you need - that might add some colour pop to an otherwise bland colour palette.

The essence of the Ivy style look is mixing the casual with the traditional. However, there is a more purely casual look commonly sported. Polo t-shirts paired with hoodies and sweaters made popular in the 90s and 00s by Abercrombie & Fitch.

Their more laidback interpretation of the preppy aesthetic moves away from the traditions to a more relaxed, beach vibe. With plaid shirts and monogrammed sweaters and baseball jackets all creating a more chilled out preppy look for the early 00s.

Pairing it all with one really bold accessory piece such as a knitted hat, shoes or scarf that really brings the whole outfit together in one fell swoop.

It can be difficult to find the balance between looking presentable and looking preppy, but it doesn't take a lot of effort. And it doesn't cost a lot of money either. You don't need to be rich or go to a prestigious university to dress preppy, you just need the right gear and the right attitude.

Preppy Aesthetic Brands

When talking about the preppy look we can't not address some of the iconic brands which have truly capitalised on this style.

J. Press

J. Press is one of the founding fathers of the preppy style, founded at Yale in 1902. It's more traditional in style, with a focussed approach on tailoring and has suits at the forefront of their offering. In recent years they have tried to modernise the brand with its use of bold, bright colour in their tailoring. Collabs with brands like Todd Snyder are a look at reviving the brand and making it current to a new generation.

Brooks Brothers

Brooks Brothers are another early founder of the preppy aesthetic movement, in fact earlier than J. Press; being founded in 1818. And are America's oldest apparel brand, not initially a 'preppy' focussed brand per se.

They're more a clothier who had been ever present in American high society; they became a staple. So it inadvertently became synonymous with America's upper classes. Which they fully exploited during the 1950's with the savvy move to open stores in the campuses of all the Ivy League schools.

Timeless looks such as the collection released for Fall/Winter ‘22 saw traditional pairings of long pleated skirts with cricket style jumpers. That classic heritage meets sportswear to get the preppy look.

This double corduroy pairing is a bold look but an interesting one nonetheless. Matched with a patterned shirt and accessorised with a belt makes for the perfect preppy look for the office.

More of a casual preppy style with the bold colour chino, black brogue and white sport sock. Layered up with a shirt base layer and classic crew neck sweater on top.

The preppy look is never short of bold colour combos. Prime example above with the pink and turquoise shirt and sweater pairing. And a camel chino makes for a very waspy look suitable for any affluent household.

Never ones to shy away, Brooks Brothers use mixed fabrics and patterns. This is a classic preppy look with the rugby shirt layered on top of a striped pale blue shirt with a quilted jacket on top. And topped off with a burgundy corduroy trouser, it's quite an eclectic mix.

Brooks Brothers' 2022 autumn winter collection didn't disappoint in terms of inspiration and bold colour use. The old adage of ‘pink and green should never be seen’ certainly doesn't apply here. Pink corduroy trousers matched with a green jacket and navy blue sweater certainly is a look but one we’re definitely here for.

Ralph Lauren

Ralph Lauren is the epitome of preppy in our opinion. The aspirational vision of the American middle class. Clean, classic designs that seem to be a staple of american fashion. Capitalising on the classic polo shirt design featuring the polo player emblem has become one of the brand's most well-known pieces. And an icon amongst 'yuppies' and 'wasps'.

It wouldn’t be Ralph Lauren without a blue pinstripe shirt and the classic navy blue blazer with an emblem of some sort emblazoned on the chest pocket. But paired with the camel chino sets the look off perfectly.

Another go-to preppy look from Ralph Lauren is the white button polo. Perfect for those summer days, it's been around for decades and will be around for decades more. Paired with white trousers is a bit of a holiday gelato disaster waiting to happen - but you could always go with a navy chino if you want to play it on the safe side.

This timeless cable knit from Ralph Lauren is jazzed up in the bold canary yellow and paired with contrast blue shorts. Perfect preppy style for those late summer days.

The same cable knit jumper can be seen here in a burnt red/orange. Interestingly paired with a denim shirt underneath and a dogtooth tweed patterned shorts. Rather autumnal vibes to this look.

Another classic ‘waspy’ look here, they look a white trouser. Matched with a racing green polo and tweed style herringbone sports jacket it's the perfect outfit to pop down to the stables in.

It wouldn’t be preppy if there wasn't the perfect woven belt to bring your ensemble together. One thing we would say about Ralph Lauren standing the test of time and remaining the more popular of the prep style brands would be in enduring quality and attention to detail with their products. Unlike some cheaper brands who come and go.

Aimé Leon Dore

A relatively new-comer to the world of preppy fashion compared to the likes of J. Press, Ralph Lauren et al. Born in 2014 this brand brings a fresh take on preppy fashion. With a focus on the sporting side of the style more than the tradition. It’s preppy streetwear has been referred to a “nu-prep” which we feel is a great description for what they are bringing to the market.

The quality of their product is higher than average for similar items and the price tag matches that. But overwhelmingly you are buying more into a brand and community with Aimé Leon Dore. With strong association with 90s hip-hop and urban culture it brings new angle to the seemingly old conventions of preppy styling.

Strong, strategic partnerships with older, established brands have really brought them to the forefront of current fashion. They are very much the hot brand of the moment, especially after winning investment from LVMH recently. Working alongside Drakes, an established traditional menswear brand definitely brought a more preppy flavour to the collection.

The more casual vibe to the brand is brought via the introduction of ice-hockey shirts, accessorised with woolly hats and scarves and the oversized casual chino.

The monogrammed overshirt is a subtle interpretation of the classic preppy style. Layered up over a denim jacket and matched with a classic NY Yankees baseball cap makes for a casual preppy outfit.

Classic colourful corduroy is a staple in the preppy wardrobe. Paired with a formal brogue and large wool coat and accessorised with a patterned scarf makes for a great look for a yuppie come Autumn winter this year.

The camel coloured wool coat is a go-to for a preppy style. With the plaid shirt and high rise, mid-wash denim jeans are a perfect casual combo. And of-course the unforgettable brogue with a sports sock is the must-have feature of this aesthetic.

Double Monogramming

The preppy aesthetic is all about Ivy League style, and one of the best ways to get that look is by double monogramming. This involves adding two initials to your clothing or accessories, usually in a contrasting colour.

Double monogramming is a great way to add a touch of class and sophistication to your look, and it's also surprisingly easy to do. All you need is a needle and thread.

Varsity Jackets

No article about the preppy aesthetic would be complete with mention of the varsity jacket. Preppy style is all about classic, clean-cut clothing. And one of the most iconic preppy pieces is the varsity jacket.

Usually made of wool with leather sleeves, a varsity jacket is the perfect way to add a touch of prep to any outfit. Inspired by school teams of Ivy League Universities during the 50s and the trend has been ever present since.

Here's how to style a varsity jacket for a preppy look.

1) Wear your varsity jacket over a button up shirt or sweater, but keep it untucked so it doesn't get in the way.

2) Wear your pants at your natural waist and tuck in your shirt

3) Wear sneakers instead of dress shoes

4) Roll up your sleeves

5) Accessorise with a scarf or knit hat and you're good to go!

It’s all in the details

One of the most defining aspects of Ivy League style is attention to detail. This can be seen in everything from the way you tie your shoes to the way you fold your pocket square. Paying attention to the small things will make a big difference in how you look and feel.

Choosing the perfect accessories

One of the most defining aspects of Ivy League style is attention to detail. This can be seen in everything from the way you tie your shoes to the way you fold your pocket square. Paying attention to the small things will make a big difference in how you look and feel.

Woven Belts

It wouldn’t be a complete preppy outfit if it didn’t feature a woven leather belt now would it… Worn by both men and women alike it's the perfect accessory for your brightly coloured chinos.

Another style has to be the ribbon styled belt. Usually reminiscent of University college tie colours it's a simple accessory that can be used to brighten up your outfit.

A style which can be sported by ladies also. As seen here with this thin leather belt.

The preppy style watch

Similar to the belt style, this usually features a striped ribbon strap. Brands like Daniel Wellington have very much capitalised on this style. Simple watches make for the perfect accessory to bring the outfit together.

Bracelets

Whilst talking about the wrist we can’t resist mentioning the preppy essential that is the Miansai anchor bracelet.

The blue braided cable interlinked through the instantly recognisable gold anchor. Clearly a nod to another affluent pastime of sailing.

Baseball caps

A staple in any preppy wardrobe, dress down an otherwise more formal outfit. Or just hide your terrible bedhead underneath it. For 2022-23 vintage 90s style washed out baseball caps are proving very popular.

Ralph Lauren have released several styles in different faded colourways this season. The washed out combo version featuring both a pale blue and mint green is a personal favourite.

Preppy style tie

In the age of working from home most don’t have a reason to wear a tie. But what is making a comeback is people dressing up for dinner and going out. Putting more effort into your evening wear than workwear does seem a bit odd but what other opportunity do you have in today's world?

And for the preppy gentleman no formal occasion would be complete without a University college style, striped tie. Inspired by the colleges of Eton, Oxford and Cambridge these stripes represent your school colours.

The ties shown above are Drakes nonetheless, the masters of pure silk ties. All handmade in England from the finest raw materials.

Eyeglasses

To get the look of a well educated Ivy League student you definitely need the perfect pair of preppy eyeglasses. Commonly associated with the ‘P3 shape’ which for those not already in the know is the round panto style frame.

This is commonly worn in a tortoise colour way. Styles found from US brand Oliver Peoples fit the bill well. The O’Malley frame is a classic waspy spectacle style, with its warm amber havana hues. The timeless keyhole bridge matches well with the classic nature of the overall preppy aesthetic.

You can ofcourse go for a squarer shape, this style features the keyhole bridge but is a softly square frame. Produced from a transparent acetate it means the style isn’t too dominant on the face, for those looking for something that's not too loud.

A wire rim is also a style sported by many preppy enthusiasts. Very much a traditional style which has made a comeback after a dominant few years with acetate. It's more subtle on the face and usually in the round panto style similar to that of the P3 shape. Definitely a style to consider if you are looking for something less in your face.

For ladies looking for that preppy look in their eyeglasses look no further than Ralph Lauren eyewear. Even though a Luxoticca licensee, the collection they produce definitely captures the essence of the preppy style.

This bold, oversized black frame from the Ralph Lauren eyewear collection is a fantastic statement pair of glasses for those looking to achieve that waspy look. Its youthful and fun styling will definitely suit almost any face shape.

Havana tortoises have the same appeal in the women's collection as they do for the men. It's a fail safe frame. You cannot go wrong when choosing a new pair of eyeglasses. This subtle cat-eye rectangular frame with gold detailing is a great choice for that preppy look.

Preppy style summary

Preppy style is all about classic, clean lines and a polished look. The key to nailing the preppy aesthetic is to keep your clothing and accessories simple and understated. But that doesn't mean you can't have any fun with your wardrobe! Add a pop of colour or pattern here and there to add some personality to your look. And don't forget the most important accessory of all: a great smile!