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Born from the ivy-covered walls of distinguished American universities and prestigious private schools of the 1950s, preppy fashion possesses a certain charm.
Its essence lies in impeccable tailoring; polo shirts, cable-knit sweaters, blazers, khakis – the classics that paint a picture of wholesome academia.
Preppy Summer Outfits
The summer preppy aesthetic witnesses high quality essentials like button-down shirts, and conservative pieces, like the loafer remixed with a platform heel for the modern era.
With crisp white shirts and white trousers, it’s the height of preppy style, mastered by sartorial preppy heavyweights Ralph Lauren and J.Crew.
Scroll below for inspo for preppy summer outfits to try out for the warmer months.
Button Down + Skirt
Embracing your scholarly side has never looked chicer.
Refreshingly, preppy outfits are one of the most long-lasting and sustainable aesthetics to emerge, due to its longevity, smart styling and and timeless appeal.
One of the easiest ways to incorporate the classic style is with a striped shirt.
Embrace the striped shirt’s nonchalant appeal, playing on the minimalist aesthetic by pairing it with a cream miniskirt for summer.
Shirt + Trousers + Loafers
There is a preppy thread that is hard to ignore when investing in a striped button down.
The height of preppy style is reached when the button down is tucked into high waist trousers and paired with loafers. The collegiate glasses are the perfect finishing touch to the sartorial style.
Shirt + Shorts
Preppy style focuses on classic pieces worn neatly. It’s versatile with a pinch of posh.
There are a myriad ways to wear the striped shirt, and for an easy preppy summer look that has a more casual undertone – roll up the sleeves and style the shirt with a pair of crisp white shorts, whether it be linen or cotton.
Finish off with preppy summer shoes – whether it be boat shoes or chunky loafers.
Button Down + Dress + Sandals
For an added layer, texture—and also much needed sun protection during those hot summer days- add a striped shirt. Wear it open and unbuttoned, or semi-closed with a belt for definition.
Flat sandals complete the toned down preppy style.
Shirt + Trousers + Sandals
Resist the temptation to pair white trousers with a bright color palette or print in favor of a preppy button down shirt.
To finish off the look, make like Blair Waldorf and never leave your head unadorned. Whether it’s with a classic head band, giant scrunchie or silk bow, more is more when it comes to hair.
A headband can prep-ify any outfit.
Button Down + Shorts + Basket Bag
Understated elegance, preppy style whatever you call it, the ultra-crisp button-up shirt transcends trends and seasons.
Styling-wise, tucking the crisp shirt into a pair of pleated solid colored shorts is your friend. To amp up the preppy factor, add oversized pearl earrings to finish off the look.
Sweater + Top + Tennis Skirt
Pleated school skirts is a preppy dress code must. This is one school-uniform style to stock up on to achieve the elements of classic preppy style.
Those pleated skirts and preppy sweaters, especially in a nautical color combination, have the power to instantly put anyone in the mood for a match, no matter the level of your tennis prowess.
Vest + Tennis Skirt + Mary Janes
If you’re looking for a way to channel the country club aesthetic, equip yourself with cool-girl takes on school uniform staples like the tennis skirt.
Add an updated pair of Mary Janes, and a waistcoat for added dimension. This is the perfect way to enjoy lunch at the local country clubs.
Jacket + Polo + Tennis Skirt
All preppy casual summer outfits need a pleated mini skirt.
This outfit lands in the sweet spot between ‘back to school’ and ‘tennis round on a Sunday afternoon.’
To achieve the preppy athleisure style, pair with a collared shirt for a trend-forward tennis outfit that is equal parts technical and stylish.
Sweater + Skirt + Sneakers
Scholarly style staples traditionally worn by the Ivy League elite—like cable-knit sweaters and cardigans are a must for preppy personal style.
A cable-knit is a preppy staple, whether it be in neutral tones or bright colors that automatically screams out “prep” school attire. Finish off the look with baseball hats that give off the same preppy vibe.
Sweater + Tee + Jeans + Sandals
For the more contemporary preppy style acolyte, wear a sweater draped over the shoulder and tied loosely at the front.
It wouldn’t be a preppy wardrobe without nautical stripes.
Polo + Skirt + Sandals
Polo shirts are the foundation of a preppy, all-American wardrobe, thanks to designers like Ralph Lauren and Tommy Hilfiger making them mainstays in their collection.
The staying power of the collared shirt is undeniable. Tuck it into a flippy skirt and wear with tube socks and loafers or sandals for a polished look.
The relaxed silhouette is a great choice for tucking into trousers.
Polo + Shorts
Polo Ralph Lauren, along with labels like Tommy Hilfiger and Brooks Brothers, practically invented prep. The summertime is the perfect time to wear their iconic Polo player and pony—the badge of all preppy fashionistas.
The structured polo is a lovely addition to white shorts – making this an easy stylish outfit utilizing easy summer clothes that a part of a preppy wardrobe.
Cardigan + Polo + Shorts + Loafers
Slip into a pair of loafers to experience the ultimate preppycore footwear. While the timeless, ivy-inspired look never goes out of style, it evolves season after season.
The different styles of the footwear make them a great way to add a finishing touch to your preppy summer outfits.
Regardless of the diverse amount of preppy clothes, loafers are a must for that preppy look.
Chunky soles with ankle high socks give your look a fashion twist while a tasseled loafer or Oxford lace-up shoes are classic preppy options.
Blazer + Trousers
For formal occasions, choose tailored styles with subtle stripes and crisp blazers.
The pairing is a perfect choice that still maintains a scholarly appeal, while having the allure of a classic summer look.
