The Top Preppy Sports and How to Dress for Them

Though the popularity of the preppy style really took off in the eighties, it is still quite trendy today among those who are active in what are generally considered to be preppy sports, with three of the top options being tennis, sailing, and golf.

Unlike more casual sports like hockey or baseball, there is more of an emphasis on fashion in preppy sports, with these activities incorporating elements of the fashion world and vice versa.

Spectators may often have their eye on an athlete’s fashion choices just as much as they do on their skill level and performance.

Perhaps you are highly skilled at these types of sports, but are you also dressed to impress? Let us take a closer look at some of these preppy sports and how to dress for them today.


What Makes a Sport Preppy?

Before we dive into individual sports, let us consider what makes these sports preppy in the first place.

When it comes to fashion, the term preppy historically refers to the typical look of a student from an expensive prep school.

So then, when we apply this to the idea of preppy sports, we are looking at the types of sports that we often associate with people who are well-off in terms of their finances.

While some of the following sports still require some expensive equipment (has anyone tried to buy a boat recently?), others can be very accessible to the masses.

The same can be said with the associated fashion. The preppy look is no longer just considered characteristic of prep school kids, and it is easily available if you know where to look.

Castaway Clothing, for example, has some perfect options for nearly every preppy sports look and individual style. Let us get into some of them now.



Tennis Player

Tennis is one of those traditionally preppy sports that is now accessible to everyone, as a lot of parks offer free use of their tennis courts, and a racket and ball do not need to be super expensive. But when tennis was first becoming popular, things were different.

In the 1870s, lawn tennis was created and allowed mostly upper-class and upper-middle-class men and women to play with each other, which was not typical of a lot of other sports. This led to the view that taking part in this sport could lead to meeting romantic partners.

In order to attract dates, therefore, men and women alike would put some thought and effort into outfits that would be both stylish and practical for the sport. Back in the day, this may have included something like blazers for men and corsets and skirts for women.

Clearly the athleticism that we see in today’s male and female tennis players was not possible in these outfits (could you imagine trying to return a serve in a blazer or corset?), so something had to change.

It was not until 1920 that French player Suzanne Lenglen caused a stir by wearing a skirt up to her calves and bare arms during a Wimbledon game.

After this landmark incident, women’s tennis dress code became more relaxed, and in the 1930s, women began to wear more drop-waist dresses and polo shirts, and these types of shirts were also now worn by men.

Interestingly, the popped collars possible with a polo shirt were used to help protect players from the sun. It was not until the 1940s that women started to wear shorts as men did on the courts, and this type of style can still be seen today.


How Do I Get Today’s Preppy Tennis Look?


Today’s preppy tennis outfit allows for a lot more movement than those in the past, and men's and women’s styles can be quite similar. Outside of the appropriately named tennis dress, perhaps a type of clothing most often associated with tennis is the polo shirt.

A women’s polo shirt and a men's polo shirt are both always safe and fashionable choices out on the courts. These can be paired with a visor to help keep the sun out of the eyes and focused on the game. If you are worried about the sun’s effects on the rest of your body, you may even consider a sun shirt to block those harmful UV rays.

Pair these with a good pair of shorts or a skirt that allow for both performance and style, and of course, a comfortable pair of your favorite tennis shoes or sneakers, and you are good to go!



Man Playing Golf

Golf is another sport that has always been well-known for its fashion. This preppy sport has been around since it was invented in Scotland around the 15th century. In keeping with the traditional Scottish style, thick fabrics like plaid or tweed were worn to help protect players from the cold weather out on the greens.

Knickerbockers, which are a type of male baggy-kneed trousers, were often made of these materials. A version of them called plus-fours, which were knickerbockers with an extra four inches in length, was also popular with golfers.

These trousers were often worn together with tweed jackets and flat caps, elements of which can still be seen in today’s golf style.

Fast-forward to around the 1920s, when golf was growing in popularity, players can be seen in two-tone shoes, long socks, knitted cardigans, and even shirts and ties. It was not until the 1930s and 1940s that preppy golf players started to move away from the knickerbockers and plus-fours and into long flannel trousers.

Golf, in general, was becoming a bit more casual at this time, so golfers started to do away with the shirts and ties and into more lightweight clothing that would help keep them cooler when out in the heat. It is this type of clothing that continues to be popular with golfers today.


How Do I Get Today’s Preppy Golf Look?


Not unlike tennis, polo shirts are still a popular option out on the greens for both men and women. Men can wear these together with a pair of pants or shorts, both of which you will often see in both bright colors and fun patterns.

These styles may also be seen when choosing a belt to help accessorize the look and perhaps a more neutral golf sneaker to tie everything together.

Women also have the option of shorts and pants for their lower halves, but they may also want to choose a stretch skirt that would also work for the clubhouse after a day out on the course.

A cute pair of preppy sneakers would also go great with skirts, pants, or shorts. Finally, men and women alike can top everything off with a baseball cap or visor to help keep the sun out of the eyes and on the ball.



Sailing Boat

Sailing has been around for hundreds of years. In fact, the fashions can be traced back to the “Jack-tars” or occupational sailors of 16th century Europe.

To protect them from the elements, these sailors wore waist-length tarred leather jackets (which would later develop into today’s more fashionable pea coats) and hats on their top halves.

Underneath would be canvas or coarse linen tunics to help make it easier to move around on the ships, and these would often be paired with “slops” or loose breeches.

In the mid-18th century, the English introduced their first official Navy uniform, which was blue and white with gold trim, and this is where the term “navy blue” was born.

Tightly knitted sweaters called ganseys or jerseys also became popular around this time to help keep these working sailors warm. There were solid colors for the naval officers, and stripes were reserved for the sailors.

Interestingly, stripes were a popular choice because they thought they were easier to see in the water if a sailor fell overboard. It was also around this time that sailing became a competitive sport and made its official debut in the 1896 Olympics.

To further encourage the sport of sailing, yacht clubs were developed to support those competitive and recreational sailors.

Perhaps a common image of a yacht club member of the time and even today would be of one dressed in a Navy jacket with brass buttons on a particularly cool sailing day.


How Do I Get Today’s Preppy Sailing Look?


Since today’s sailors for sport do not usually go out in the type of weather that would require significant protection from the elements, a summery look is common and appropriate when out on the water.

Again, for any preppy sports look, you cannot go wrong with men’s and women’s polo shirts – try them in a striped style for a little more of that classic sailor look.

These can be paired with some fun and colorful shorts, which you can also get in some more nautical patterns like these anchor-print shorts for women or shark-print shorts for men.

If you like to jump overboard and get out swimming on a warm sailing day, you may want to forgo shorts entirely and wear a swimsuit, preferably a quick-drying one, so you are not stuck in cold, wet shorts for the duration of your trip.

If things do cool down when you are out at sea, though, a nice fleece-lined quarter zip sweatshirt is the perfect choice for both men and women. Pair these with a preppy waterproof deck shoe, and you will be ready for your next sailing adventure.


Well, I Am Ready To Go - But What About the Kids?


All the preppy sports clothing items listed would also be perfect for those days when you indulge in your favorite sports with your kids, but what are they going to wear?

Preppy sports styles are also very accessible for the kids, with shorts for both boys and girls available in colors and patterns very similar to those for the parents.

The same goes for polo shirts, which, as we have seen, are a must-have for just about any of the top preppy sports. And for those cooler days, a surf popover shirt is the perfect layer to add for boys and girls alike.

 So, there you have it! We have looked at just three of the top preppy sports and how to look your best while not compromising performance.

Castaway Clothing has many of these items available in many different colors and patterns. If none of the ones listed work with your style, please browse their website for more fashionable preppy items.

Whether you are hitting balls in the courts, putting on the greens, or sailing on the open seas, Castaway Clothing can provide everything you need for your favorite preppy sports.

1 comment

  • Alina Duvall

    Thanks for writing this amazing blog for us. I love to read it.

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