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Coastal Destinations with Preppy Style

The “old money” aesthetic, or in other words the preppy style, has had its place in fashion for every decade of this past century, and the current one is no exception! In our article, we guide you through the rise of preppy style and its impact on pop culture all around the world. In the second part of the feature, we introduce you to coastal travel destinations in the U.S. and in Europe that are influenced by the preppy style.

Coastal destinations with preppy style

From the most popular 90s TV shows and movies to today’s social media boom, old money aesthetic and preppy style has been a constant trend. The hype is even real for Generation Z, which is not exactly considered the easiest target group to be impressed by anything. One major factor in achieving the preppy style feeling are the preppy style destinations. Here we have gathered the most popular places we know thanks to TV series and movies. We‘ve also compiled some hidden gems that definitely have a touch of a preppy lifestyle.

The origin of the preppy style

The initial preppy style emerged in the US around 1910-1912, from the mid1940s onwards known as Ivy Style. One of the first and most iconic preppy brands, J. Press, developed fashion collections that were sold exclusively to various colleges of the Northeast US. It is widely believed that this very label helped to shape the preppy culture as we know it today.

In the 1990s, the preppy aesthetic peaked in popularity as it became mass-market. While the clothes still held a sign of privilege, they became available to the masses thanks to the rise of brands such as Tommy Hilfiger, Calvin Klein, and Lacoste.

The new era of preppy style


So, when and where did the real popularity start? Maybe it was the corduroy or tweed blazers, Oxford shirts, plaid skirts, Argyles sweaters, Nordic vests, and knee-high socks worn by Cher Horowitz in the ‚90s hit Clueless. Or perhaps in late 2007, when Serena van der Woodsen and Blair Waldorf – the two leading ladies of the U.S. series Gossip Girl – helped the style gain new popularity when they first hung out on the steps of the Met in New York in classic blazers, button-down shirts, short schoolgirl skirts, and iconic hairpieces. It‘s hard to say, but they quickly became the epitome of upper-class chic, where preppy style meets elegance and college chic. Little did they know then that their fashion style would still be a must-have more than a decade later. Beyond the beautiful and instantly recognizable preppy style apparel, these phenomenal pop culture screen moments have also played an integral role in making some places around the globe the ultimate symbols of the style. It‘s not just about fashion but something broader and greater – like establishing a lifestyle.


Coastal destinations?


When we think of preppy-style destinations, most of us subconsciously imagine a place near the water. That is quite simply because the clothes are inspired by traditional preppy lifestyle activities such as sailing and rowing. The coastal vibe is deeply rooted in the design, making the garments reflect these leisurely pastimes. Therefore, coastal destinations are places that share a deeper connection to preppy style than you might think at first glance. No wonder coastal destinations like the legendary Hamptons or Palm Beach became the symbol of preppy style. Although the Hamptons have quite a hype associated with the privileged lifestyle, it‘s far from being the only destination that can be identified with the preppy-inspired life. Here, we‘ve rounded up some well-known and lesser-known coastal destinations and hope to inspire you to pack up your cable knit sweater and tweeted blazer and experience your preppy vacation.

The United States and the coastal preppy destinations


We begin our preppy journey at the far east end of „Long Island“, in the „Hamptons“ – probably the first association everyone has when thinking about the preppy style. The Hamptons is the ultimate preppy symbol not only for Americans, but for the entire world. Known for its beaches and art museums to hedges that grow taller than summer temperatures, this place is the epitome of a stylish and exclusive aesthetic. Although the Hamptons are known as a stomping ground for the rich and famous, there are plenty of places where regular people can enjoy themselves. Among them are stunning beaches, casual restaurants serving quality seafood, and charming guesthouses for lodging.


Scottsdale, Arizona, is a great place for a Preppy-style vacation. With its luxurious resorts and classy boutiques, it has everything you need in order to feel the atmosphere of this style and its exclusivity. The place is often visited by the old money families, who represent the preppy style, as many of them have real estate there. And who knows, maybe you will spot some of them in person and get inspired for your next outfit.


The state of California is the right place for your chic destination as well. Several locations pop into one’s mind. However, San Francisco is probably one of the most prominent. The area of the city is urban and ultra-trendy, where streetwear is chic but comfortable. Vintage clothes are in as well as sleek, contemporary casual styles. You can see all sorts of preppy garments here.


Hawaii and Honolulu are not to be missed. Apart from being very trendy destinations due to their neat street style, they also offer the typical activities that the proponents of preppy living enjoy. Sailing and rowing are just some of the recreational activities you can indulge in.


Your preppy destination guide of Europe


Europe has a whole range of upscale destinations to offer. Starting from the west of the old continent, France and the French Riviera are the first places that come to mind. The most popular cities Nice, Cannes and Saint-Tropez are full of luxury hotels and boutiques. They generally have the preppy aesthetic and are the perfect place to see that style roaming the streets. Nevertheless, one should be careful when taking inspiration from it because the preppy looks in France are strongly influenced by another fashion trend – French chic. The two should not be mixed.


Deauville in Normandy is best known for its beautiful beaches, luxury hotels, and high-end stores. Because of its proximity to Paris, it is often referred to as the Paris Riviera due to attracting the capital‘s upscale crowd. As a center of French culture with many annual events such as film festivals, classical music concerts, and polo matches, it fits very well into the preppy lifestyle. A curious fact about the place is that Coco Chanel used to spend her summers here.


The UK & the preppy style vibe


Crossing the English Channel, we can‘t help but point out some fancy destinations in the United Kingdom like Brighton and Eastbourne in the south of England. Both spots are influenced by the preppy lifestyle. With water activities, chic fashion, great beaches, and restaurants, it‘s impossible to escape the preppy vibe.


The county of Cornwall has a particular appeal that relies heavily on preppy. Moreover, they have an iconic brand related to the lifestyle – the Seasalt of Cornwall. It is not a surprise that Cornish residents often wear garments made by the brand, embodying the typical style of the preppy trend. In addition, the area is by the water. With this, it ticks even more boxes as a preppy-style destination.


A romantic stroll along one of Torquay‘s beaches is simply a dream. Located on the English Riviera, Torquay is most famous for its beaches, which offer the best sea swimming, paddling, and kayaking. And what about fashion? You will notice some button-up shirts, tweed blazers, boat shoes, and preppy cable knit sweaters.

Germany and its coastal preppy outlook


Returning to the home of sisterMAG – Germany – we cannot miss the northern part of the country. The area, which used to belong to the Hanseatic League in the Baltic region, is influenced by the preppy scene. Rostock, Hamburg, and the island of Rügen are typical examples of destinations in Germany inspired by the style. Stripes, Oxford shoes, chino shorts, and loafers are the effortless chic that rules the streets. The whole aesthetic is complemented by the location and architecture of the surrounding area.


The island of Sylt is like the sophisticated German twin of the Hamptons. It is often referred to simply as the German Hamptons and offers everything that can be seen and experienced in the American original. For many Germans, the island of Sylt is the hottest place for their summer vacation and offers a wide selection of cozy beach restaurants and water sports activities. However, what is a must if you want to blend in with the preppy surroundings is the beach walk in your Barbour puffer jacket, which you should not miss.


Plan the preppy getaway!


The preppy style is much more than just that. It is a way of life that is worth experiencing. Try your hand at preppy style but steer clear of thick logos and flashy designer pieces. Even if you don‘t dig deep into your wallet, you can still imitate this style with inexpensive basics. Hopefully, this short journey through some of the most iconic places has inspired you to take your next vacation in a preppy location and live your own preppy-style fairytale.


For even more interesting facts about England’s seaside towns, check out our Cultural history of the beach holiday.