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The Best Preppy Summer Outfits for 2021

Posted May 18 2021

Best Preppy Summer OutfitsWe think we can all agree that preppy fashion is not only a trend but also a way to express your personality through pops of pastel color and bold prints.

Preppy fashion is from a time where preppy was not as much a fashion choice but a lifestyle. This was when ivy league schools seemed to rule, and upper-middle-class boys and girls went to school in these tidy yet expensive clothes.

 However, the preppy look has now become a fashion choice over a particular lifestyle. It reminds us of all the many summer activities that it’s styled after (golfing, sailing, playing cricket, and tennis, to name a few!).

Even though the preppy style exploded in popularity in the ’80s, it is still very much in fashion today, offering up the hottest looks for summer of 2021. Let’s take a look at the best summer outfit inspiration for the season.

Preppy Summer Outfit Staples That You Need In Your Wardrobe Right Now

Looking for preppy summer stables that can be mixed and matched to create an endless amount of perfect summer outfits?

We’ve gathered some of our favorite preppy summer outfit staples for both men and women that can be mixed and matched or worn on their own to create the best preppy summer outfits that will never go out of style.

Embroidered Shorts


Embroidered Shorts

Embroidered shorts are a seriously fun trend for both men and women, which truly lets you show off your personality!

This summer, we’re seeing both bright and pastel-colored shorts embroidered with everything that reminds us of the season - we’re talking palm trees, crabs, and lobsters, not to mention martini glasses and beer pong.

 Yes, beer pong-themed navy blue shorts do exist, and we could not be more excited about it! While embroidery is certainly not limited to preppy clothing, it has significantly impacted the preppy outfit staple, the polo.

Pair your embroidered shorts with a solid colored polo or long-sleeved cotton shirt to let your embroidery have the spotlight.

Flashy Flamingos

Flashy Flamingos

The flamingo has found its way into preppy summer fashion, which makes sense - after all, flamingos are a gorgeous shade of pink that is comparable to the pastel pink found in preppy summer clothing.

Plus, what’s not to love about flamingos? So, what’s the best way to pull off this statement, tropical bird?

 Opt to wear your flamingos in the form of embroidery on a pastel blue pant or skirt, or go bold and splash them all over your swim shorts.

Don’t feel like adding a flamingo printed pant to your wardrobe? Consider a flamingo tie or a pair of dangly earrings to add some personality to your outfit!

Nautical Style

Nautical Knots

A nautical color combination will never go out of style when it comes to preppy summer outfits, and in fact, it dates back to the original ivy league style.

There are a number of ways that you can make this navy and white nautical statement, including the classic navy and white striped shirt with a pair of crisp white shorts or pants.

 If you don’t feel like dressing head to toe in these classic nautical colors, you can opt for a navy nautical style belt (this one’s complete with capitalistic pig!), or you can grab a white and blue knotted tote bag to throw all of your earthly possessions in.

Go To Hell Pants

Go To Hell Pants

No, we’re not trying to flip you off - Go to Hell Pants are a popular preppy trend that can often be seen out on the golf course!

Go to Hell pants are technically any boldly colored pair of trousers, with or without a pattern or motif.

This includes the popular madra pattern and printed or embroidered motifs. So, why the harsh name?

 Go To Hell pants originated in the mid-1970s, which detailed the starkly opposite habits of America’s East Coast elite in and out of the workplace.

While opting for plain, traditional clothing in the office, men of privilege would let loose with their clothing after work, often while playing golf, drinking cocktails, and/or talking sports in their off-hours, particularly at country clubs and at ritzy vineyard estates.

 Author Tom Wolfe described the trousers that these men would wear as “checks and plaids of the loudest possible sort, madras plaids, yellow-on-orange windowpane checks, crazy-quilt plaids, giant houndstooth checks, or else they were a solid airmail red or taxi yellow of some other implausible go-to-hell color.”

This Go to Hell nickname stuck and has remained a popular summer trend in the preppy aesthetic since!

Collared Shirts

Collared Shirts

A collared shirt doesn’t just necessarily mean the classic polo (although we’re not going to say no to a good pastel-colored polo), with the Oxford button-down and the seersucker shirt both being preppy fashion staples.

The classic polo shirt has been in existence since 1896, after John E. Brooks of Brooks Brothers returned from a trip to England.

While visiting the country, he spotted the affixed button-down collared-shirts that polo players wore and brought the outfit idea over to the United States.

The “Original Button-Down Polo Shirt” debuted shortly after. Collared shirts can be found in every color of the rainbow, with nautical embroidery being a popular addition to these items of clothing.

The Navy Blue Blazer

Navy Blue Blazer

The navy blue blazer is a trend that will quite literally never go out of style and brings the classic nautical summer vibes that are associated with preppy style.

This navy blue staple can easily be dressed up, down, or accessorized and is a perfect addition to both men’s and women’s wardrobes.

 While the right fit men’s blazer should not be oversized and should hang straight down without being too restrictive, an oversized blazer is a great fashion statement for women.

Whether purchasing a navy blue blazer in a larger size, purchasing a men’s blazer, or opting for a blazer that is already made oversized, an oversized navy blue blazer is the perfect addition to an otherwise all-white outfit.

If you’d like to jazz up an otherwise plain navy blue blazer, you can try this red and white stars embroidered blazer.

Preppy Summer Shoes

The right shoes are the key to pulling together any outfit - and what is more quintessentially preppy than the boat shoe?

The boat shoe is one of the most prominently seen casual shoes in summer resort towns, making it the ideal addition to your preppy summer outfit.

 Classic boat shoes are generally seen in black or brown leather and can often be seen with a super nautical bearing accent. Jeweled sandals are also one of the top-selling shoes for summer, complimenting the preppy summer style by adding a little something extra.

 While sparkle sandals have been in existence for quite some time, every outfit could use a little bit of sparkle! Jewelry is the classic choice for glamming up your look, but we love the trend of shimmery sandals and other preppy summer shoes.

Our Anna Jeweled Sandal is one of our top-selling shoes for summer, and it’s easy to see why: covered in gorgeous gemstones, these shoes put the perfect finishing touch on any summer outfit.

For a beachy vacation or a day lounging by the pool, slip on these waterproof sparkle Jack Rogers jelly sandals.

Outfit Accessories

What would a preppy summer outfit be without accessories? If you don’t wish to opt for the in-your-face patterns and prints of the above-mentioned “Go to Hell” pants, you may wish to consider adding to this conservative look in the form of bow ties, skinny ties, pocket squares, and lapel pins.

Fun prints add a little something extra to an otherwise super clean and simple look and are a great way to add just that little bit of personality to your outfit.

If you’ve gone the opposite route and your outfit looks a little bit busy with colors and patterns, this would be a time to add an accessory in pastel or a white to finish off your outfit.

Getting Your Preppy Wardrobe Summer Ready

It’s important to remember that there is no specific rulebook when it comes to preppy fashion (unless, of course, you’re looking to meet the dress code for a golf course or country club!).

No matter your style, having fun and feeling confident should be number one on your list of fashion priorities.

If you like the preppy style but don’t want to jump into it all at once, you can never go wrong with a classic white polo, a pair of tan pants, and some great leather boat shoes.

Slowly build up your preppy summer wardrobe from there by venturing into pastels, and before you know it, you’ll be donning your first pair of madras pants!

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