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Achieving Preppy Elegance for Elevated Outfits this Fall

Samsung C&T Global PR Manager

Preppy fashion is making a strong comeback this fall, offering endless styling options with Ivy League-inspired classics like blazers, cardigans, rugby tops, and pleated skirts. With its rich history, preppy style remains effortlessly chic, blending comfort with sophistication in both daily wear and office looks.

A triptych image showing three models in preppy fashion outfits. On the left, a model wears a charcoal wool pleated skirt by Maïs, paired with a dark grey top and black loafers. In the center, a model wears a khaki micro skirt and oversized white shirt with big pockets by Kuho Plus, standing with her hands in the skirt's pockets. On the right, a model wears a check tweed jacket and matching mini skirt by JOY GRYSON.
Left: Maïs Round York Wool Pleated Skirt in Charcoal; center: Kuho Plus Micro Skirt Paired with the Essential Big Pocket Shirt; right: JOY GRYSON Check Tweed Jacket and Mini Skirt

Preppy fashion is having a moment this fall with the return of classic Ivy League-inspired blazers, cardigans, rugby tops, and understated yet chic accessories. Transitioning into a new season is the perfect time to try new looks and reinvent yourself for your autumnal era.

Let’s delve into a brief overview of preppy fashion’s history and find inspiration for our fall wardrobe for 2024. Trending at Samsung C&T’s Fashion Group are striped patterns, plaid designs, pleated fabrics, and oversized rugby sweaters—essential preppy staples that offer endless styling possibilities

Beyond the Blazers: How Did Preppy Style Evolve?

Preppy style is a trend that continues to reinvent itself, all while maintaining its aristocratic roots. According to a podcast series on “Articles of Interest,” “Preppy” style dates back to the days of the ‘Bright Young Things’ in 1920s London and the ‘Ivy’ aesthetic of Princeton students wearing their sports attire to dining hall dinners. The allure of preppy clothing comes from its simplicity and its effortlessness while maintaining a very wealthy and modern aesthetic.

In 1965, Japanese author Shosuke Ishizu chronicled the delights of American Ivy fashion in the now-coveted book “Take Ivy.” This book sparked a wave of preppy trends in Japan and heavily influenced modern Japanese fashion. The 1980s were when “prep school” fashion became mainstream, as documented by the book “The Official Preppy Handbook,” by Lisa Birnbach. The book showcased both preppy style and preppy lifestyles, including sports to play and food to eat to accompany your preppy style.

Today, preppy styles are the signature looks of many brands, including Thom Browne, Brooks Brothers, and Polo Ralph Lauren, and appear on runways and high streets in the form of sporty motifs, pleated seams, and plaid patterns.

Daily Uniform

The pop culture icons who made prep school uniforms stylish include Chuck and Blair from Gossip Girl, Cher from Clueless, and Rory from Gilmore Girls. Each season, elements of these uniforms, such as pleated skirts, neckties, and blazers adorned with embroidered emblems and trimmed pockets, are reinterpreted in clothing pieces for the everyday.

This fall, midi-length pleated skirts with thin leather belts, crisp cotton button-down shirts, and blazers are all making a sophisticated comeback. These preppy items can be mixed and matched for endless style combinations. Pleated skirts look great paired with soft cardigans and loafers for a more casual uniform aesthetic.

Two images showcasing preppy fall looks. On the left, a model is wearing a khaki micro skort with a matching tailored blazer by Kuho Plus, standing with one hand in her pocket. The model on the right is wearing a black textured cardigan jacket by 8 Seconds and a black plaited skirt.
Left: A Kuho Plus look for fall featuring a khaki micro skort and matching blazer; right: Black cardigan jacket by 8 Seconds
On the left, a model wears a Maïs charcoal grey wool pleated skirt paired with mary jane shoes and white socks, creating a classic uniform-inspired look. On the right, another model sports a Juun.J grey short-sleeved V-neck pullover over a blue collared shirt, with matching tailored trousers, embracing a minimalist, clean-cut aesthetic.
Left: Maïs charcoal wool pleated skirt paired with mary janes; right: Juun.J short sleeve v neck pullover in grey
A split image showing two male models. On the left, the model wears a preppy checkered sports jacket from Beyond Closet in dark tones, paired with a navy polo shirt, light beige trousers, leather gloves, and a navy cap with 'CB' embroidered. On the right, a model sits on a red sofa reading a book titled "String Theory," styled in a casual yet refined grey cardigan from 8 Seconds over a white button-down shirt, light wash denim pants, and black-rimmed glasses.
Left: A preppy Beyond Closet check sports jacket; right: A stylish grey cardigan by 8 Seconds

Prep for Success: Preppy Looks for the Office

If there were ever a place to play around with preppy looks, it’s at the office. Commuting to your office in a casual yet sophisticated outfit is the ultimate goal for the days when you’re not feeling adventurous. Structured blazers, trench coats, tweed fabrics, simple striped cardigans, and matching preppy accessories can be worn for an elevated work outfit. Opting for understated and high-quality basics when you shop will help you look put-together and polished when rushing to throw an outfit on before work.

A split editorial image featuring two models. On the left, a model wears a striped ivory cardigan by 8 Seconds, styled with a black pleated mini skirt, hands in her pockets. On the right, another model walks confidently in a Kuho Plus trench coat layered over a blue top and beige wide-leg trousers, with a light beige sweater tied around her waist.
Left: A timeless striped ivory cardigan by 8 Seconds; right: Effortless Kuho Plus trench coat styled to perfection
Split image of two preppy office looks. On the left, a female model wears a JOY GRYSON tweed co-ord featuring a structured checkered jacket and matching mini skirt. On the right, another female model stands in a minimalist, timeless black tunic from 8 Seconds, layered over a white shirt and paired with black ankle boots.
JOY GRYSON co-ord tweed jacket and mini skirt; right: A timeless tunic from 8 Seconds.

Effortlessly Chic: Styling Loafers and Mary Janes

With comfort and ease central to preppy style, it’s no wonder that preppy footwear also emphasizes practicality and comfort. Saturdays at the boat shed or attending polo events call for boat shoes, flat Mary Jane sandals, and chic and understated trainers. Styling a comfortable boat shoe with a crew sock, striped details optional, is the ultimate preppy footwear choice. Mary janes are classic and elegant shoes that we are seeing all over our social media feeds. Understated leather loafers offer sleek and effortless sophistication and are easy to slip on in the morning.

A side-by-side image of two female models. On the left, the model wears a preppy fall outfit from 8 Seconds, featuring a beige cardigan over a black polka-dot blouse, paired with a pleated grey midi skirt, grey knee-high socks, and black loafers. She stands casually by a wooden wall, holding a phone. On the right, the model stands against a plain white background, wearing a black sleeveless dress layered over a grey long-sleeved top, styled with grey knee-high socks and black loafers from Kuho Plus.
Left: 8 Seconds fall outfit embodying preppy fashion with a pleated grey midi skirt, black loafers, and a beige cardigan; right: Kuho Plus knee socks paired with black loafers.

Game On: Sporty Looks from the Field

As we celebrate the end of another Summer Olympics and Paralympics season, we can continue to reminisce about the incredible fashion on and off the fields in Paris this year. Preppy fashion began with quintessential Ivy-League sports such as golf, lacrosse, rugby, rowing, equestrian sports, and tennis. Similarly with the “Blokecore” trend, inspired by 90s soccer players, preppy sports looks are designed to be worn on and off the field. The versatility of striped rugby sweaters, joggers printed with the name of your alma mater, and polo shirts allows for comfort in almost any scenario without compromising your style.

A side-by-side image showcasing preppy sportswear. On the left, a male model is dressed in a light blue Beanpole Men’s Supima cotton t-shirt with a striped jumper casually draped over his shoulders, paired with dark denim jeans for a laid-back yet refined look. On the right, a female model sports a red Beanpole Golf polo with a matching red plaid pleated skirt, accessorized with a red visor, red-and-white socks, and white sneakers.
Left: An elevated Beanpole Men’s Supima cotton t-shirt paired with a striped jumper over the shoulders; right: Look no further for a preppy look for the golf course with Beanpole’s Golf range.
A two-part image featuring preppy fashion staples. On the left, a female model wears an Our Hope rugby-style sweater with green and grey stripes, tucked into a high-waisted beige midi skirt, achieving a vintage-inspired preppy look. On the right, another female model is dressed in a blue-and-black striped rugby top with embroidered details from Maisonmarais, styled over black shorts.
Left: An Our Hope striped vintage-look rugby sweater paired with a classic preppy midi-skirt; right: Maisonmarais embroidered rugby top.

Stay Ahead of the Curve

Preppy fashion has evolved into many unique subgenres and trends, including coastal grandma, dark academia, blokecore, and quiet luxury. Elements of preppy and Ivy fashion can be found in many of the trends we see today, making this piece of fashion history accessible to a wide range of people. Samsung C&T’s Fashion Group, South Korea’s leading fashion company, is known for creating stylish trends that prioritize customer needs. Discover more styling inspiration and explore unique preppy looks at the SSF Shop.

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