Preppy Aesthetic
Preppy aesthetic, Preppie, or Prep (all abbreviations of the word preparatory), is the elitist subculture of America’s upper class.
In the United States, preppy is associated with the style of Northeastern college preparatory institutions. It can also denote a person who fits the mold of students or alumni of these schools.
It is a lifestyle that taps into the rich cultural tradition of America’s wealthy elite. Its unchanging scholarly sophistication celebrates timelessness and nostalgia.
What Is Preppy Aesthetic?
Preppy is an Old Money style of dress, design, and culture.
Characteristics that define preps include a specific type of educated speech, vocabulary, etiquette, mannerisms, and dress, which reflect an upper-class upbringing.
Unlike the novelty-seeking fashions of the nouveau riche, prep favors simple, understated, and never-changing clothes that exude effortless elegance and signal status.
Preppy aesthetic is defined by crisp button-downs, loose pastel knitwear, Polo shirts, and boat shoes (often without boats). It conveys the carefree, trust-fund vibes of Ivy league school boys.
Along with Nerd, Jock, and Goth, Prep, is one of the four main stereotypes used to classify high school students.
- March 26, 2023
- Dagmara Mach
PREPPY AESTHETIC HISTORY
Where Did Preppy Aesthetic Come From?
Preppy aesthetics emerged alongside the establishment of America’s first prep, or preparatory, schools in the late 18th and early 19th centuries.
These prep schools were established with the purpose of preparing students for admission to prestigious universities such as Harvard, Yale, and Princeton. They emphasized traditional values such as honor, duty, and sportsmanship. Their graduates went on to attend Ivy League colleges and enter elite professions.
The Evolution of Preppy Style Throughout History
Here are some notable developments in the evolution of preppy style:- 1920s-1930s: Preppy style began to emerge during this time period, as more students from elite New England universities began to adopt a distinctive style. This style was characterized by tailored blazers, oxford cloth button-down shirts, khaki trousers, and loafers. This style was functional and comfortable, but also elegant and understated.
- 1940s-1950s: During this time, preppy style became more widespread and began to be associated with the Ivy League look. The style was still classic and timeless, but became more refined and tailored. Blazers and sport coats became more structured and fitted, and accessories like ties and pocket squares became more popular.
- 1960s-1970s: The Kennedy family popularized preppy style during this time, and it became associated with a more casual and laid-back aesthetic. Sweaters, cardigans, and polo shirts became more popular, and the style became more colorful and playful. The influence of the counterculture also began to be seen in preppy style, with the adoption of items like denim jeans and sneakers.
- 1980s-1990s: During this time, preppy style became more associated with wealth and status, with luxury brands like Ralph Lauren and Tommy Hilfiger incorporating preppy elements into their designs. This period saw a return to the more traditional elements of preppy style, with classic items like blazers, oxford shirts, and loafers being popularized again.
- 2000s-present: Preppy style has continued to evolve in the 21st century, with a focus on sustainability and ethical production becoming more important. Classic items like blazers, oxford shirts, and khaki trousers are still popular, but there is also a trend towards more relaxed and comfortable clothing. There is also a trend towards incorporating preppy elements into streetwear and athletic wear.
Preppy Aesthetic Visuals
The Preppy visual aesthetic is deeply rooted in upper-class society and its affiliation with Ivy League universities such as Harvard, Princeton, and Yale.
The visual elements associated with the Preppy aesthetic are often broken down into two variants, New England Prep or East Coast Prep and Southern Prep, each with its own unique patterns, colors, and motifs.
New England Prep or East Coast Prep
New England Prep or East Coast Prep draws inspiration from the nautical world, incorporating elements like anchors, compasses, ships, lighthouses, whales, and maritime stripes into its design.
Hydrangeas, which are commonly found on Nantucket, are also associated with East Coast prep.
The colors used in New England Prep are derived from nature, including olive green, navy blue, beige, tan, and dark red, evoking a sense of calm and serenity.
Southern Prep
In contrast to East Coast Prep, Southern Prep is more playful and vibrant. Southern Prep incorporates elements like palm trees, elephants, monkeys, and zebras.
Lilly Pulitzer is a popular brand that epitomizes Southern Prep with its colorful patterns and prints.
The colors used in Southern Prep are much brighter and more saturated, including hot pink, kelly green, lime green, bright yellow, turquoise, and orange.
Contrasting colors are often paired together, such as pink with green or blue, orange with green or blue, red with blue or green, and yellow with blue or turquoise. Shades of purple, including lavender, are not commonly used.
Southern Prep is more casual than New England Prep, with bare arms and legs being more commonly displayed.
Preppy wallpaper, whether it’s for your phone, tablet, computer, or an actual wall can take a variety of shapes and forms.
From Lilly Pulitzer style patterns to nautical style, beautiful pink beaches, and preppy dogs, preppy aesthetic phone and desktop wallpapers give you many cute options but should generally correspond to the time of year.
Preppy room wallpapers should be more muted, incorporating neutral or pastel pallets, and simple, classic patterns such as maritime strips, paisley, herringbone, or muted floral prints.
Preppy Style & Fashion
Do you ever wish you could channel the effortless elegance of a classic 1950s movie star like Marylin Monroe or a charismatic Ivy League leader like JFK?
Preppy fashion is a polished, slightly androgynous fashion trend with roots that date all the way back to the 17th-century argyle sweater fashions of Scottish Highlands clans.
Developed by students of Ivy League universities in the Northeast in the 1950s, the preppy style has gone in and out of fashion through the years.
Brands like Brooks Brothers, J. Press, Ralph Lauren, Lacoste, J. Crew, and Vineyard Vines, define Preppy Aesthetic.
Inspired by outdoor activities such as sailing, tennis, and golf, Preppy fashion emphasizes practical layering with freedom of movement, a sense of refinement, elegance, and good taste.
The original preppy aesthetic is the New York and northern Ivy League version, which stays true to its British and Scottish roots. This style represents a love of privilege, a commitment to education, and an appreciation for outdoor activities.
The classic northern style of prep is very Dark Academia. It features darker, natural tones like hunter green, navy blue, and burgundy, paired with lots of wool, and leather, favoring tweed blazers, riding boots, and wool hats.
For example, when my bestie Gwen attended Millbrook and Lawrence Academy (northern prep schools) from 2004 to 2008, Ralph Lauren’s Rugby collection was the most popular style of preppy clothing.
Preppy clothes may help you look and feel classy, but most importantly they’ll allow you to blend into a community of like-minded peers and mentors who share your passion for knowledge, exclusivity, and a classic style that screams “I’m wealthy” without begging “rob me.”
Buying sustainable, high-quality clothing from trusted brands that have been around for decades, embraces timeless shared values like quality over quantity and the importance of pristine craftsmanship.
Accessories and Details that Complete the Preppy Look:
A preppy outfit isn’t complete without the right accessories and details.
Classic watches, leather belts, patterned ties and scarves, pearl earrings or necklaces, and classically framed sunglasses complete a preppy look.
Pay attention to the details of your outfit, such as tucking in your shirt and rolling up your sleeves for a polished and put-together look.
Women’s Preppy Fashion
Women have many more options when it comes to preppy fashion. According to my BFF Gwen, who, in her heyday attended two boarding schools (Millbrook and Lawrence Academy), and later got her masters in Milan – this is what preppy boarding school dressed like from 2004 to 2008, since Preppy aesthetic literally NEVER changes, you can still count on her advice.
Preppy women’s fashion includes variations of white button-downs, pleated skirts, A-line skirts, tweed mini skirts, V-neck sweaters, cardigans, blazers, and tennis dresses. Denim, conservative necklines, and layers of high-end luxury fabrics with classic, traditional cuts are also crucial.
Preppy women’s shoes are versatile and stylish year-round. Spring shoes include Mary Janes, sandals, espadrilles, loafers, boat shoes, ballet flats, canvas or leather sneakers, ankle boots, oxfords, riding boots, knee-high boots, and duck boots.
Mary Jane shoes are a type of low-heeled leather shoe with a closed toe, a strap across the instep, and a buckle or button closure. The name “Mary Jane” comes from a comic strip character named Mary Jane who wore shoes with a similar style in the early 20th century. Since then, Mary Jane shoes have become a classic, comfortable, and versatile shoe with a feminine touch that can be dressed up or down, depending on the occasion.
Boat shoes, or deck shoes, are a type of preppy casual footwear originally designed for use on boats and other watercraft. They typically have a rubber or non-marking sole that provides excellent traction on wet surfaces, as well as a slip-on or lace-up design. Boat shoes feature a moccasin-like construction, with a leather upper that is stitched to the rubber sole. The leather upper is often treated with water-resistant materials to help protect against the elements. Comfortable, durable, and versatile, boat shoes can be worn with a variety of casual outfits, such as shorts, khakis, and jeans, and are generally paired with sockless feet. Boat shoes are a staple of preppy and nautical-inspired fashion.
Gwen's Advice from Boarding School in the 2000s
Men’s Preppy Fashion
According to my husband, an OG 90s prep school boy from Charlotte, a man’s polo shirt game is the key to success in the preppy aesthetic. Also, a real man needs at least 10 different Polo shirts in varying colors, patterns, and animal logos. A preppy polo shirt can feature one of the three animal patch choices.
The two classic choices are the Horse (Polo), and the Alligator (Lacoste). The newer Millennial prep option is the Whale, which belongs to Vineyard Vines and hit the scene in 1998.
Though different cuts and styles of polo shirts exist, at its core, the polo remains a pull over shirt with a collar and two or three buttons at the top. Within that definition, Polo shirts offer a lot of style choices that are unique and yet all look the same. Thus, according to my husband, a preppy man’s aesthetic is all about the nuance of his panache.
Polo shirts are versatile and can be worn with a variety of clothing items, such as over-the-neck sweaters and cardigans.
In the early to late 2000s, a popular trend among men was to layer two to three different colored polo shirts, creating a unique and eye-catching look.
Patterned button downs with crisp white collars, vests, sweaters, sweater vests, navy blue cardigans, blazers and classic trousers are also crucial to the preppy look.
Needlepoint belts, Sperry boat shoes, Gucci loafers, leather sneakers, and blazers all complement this look.
According to my prep school insider husband, Northeastern rich is the preppiest prep, vintage prep, if you can get it in good condition, is supreme, and your brother’s old button down is where it’s at.
Smathers & Branson
Dancing Bears
Needlepoint
Belt
Like Preppy fashion, Preppy interior design is classic, tailored, and refined. Traditional decor of the American East Coast elite is a staple component. Through a mix of vintage and contemporary elements, the style emphasizes a sense of elegance, sophistication, and quality.
Preppy visual elements include a color palette of pastels and neutrals, classic patterns such as plaids, stripes, and florals, and elegant furniture pieces such as wingback chairs, chaise lounges, and tufted sofas.
In terms of layout, Preppy interior design focuses on symmetry and balance, with a focus on creating a sense of order and organization.
Incorporate antiques and vintage pieces, such as Persian rugs, silver candlesticks, and crystal chandeliers, to create a sense of history and tradition. Use bookcases, built-in shelving, and cabinetry to display art, photos, and cherished collections.
Color Schemes:
One of the key elements of preppy home decor is a classic color scheme. Think navy blue, hunter green, burgundy, and crisp white. These colors can be incorporated into your design in a variety of ways, from painting your walls to adding throw pillows and blankets to your couch. For a truly preppy touch, consider adding some plaid patterns, which are a hallmark of the preppy aesthetic.Furniture and Accessories:
When it comes to preppy home decor, it’s all about classic, timeless pieces. Look for furniture made from natural materials like wood and leather, and opt for accessories like brass lamps and bookends to add a touch of sophistication. Additionally, don’t be afraid to mix and match different textures and patterns to create a cozy and inviting space.Nautical Touches:
Another hallmark of the preppy aesthetic is a love of all things nautical. You can incorporate this into your home decor by adding elements like anchor motifs, rope accents, and sea-inspired artwork. Try incorporating some vintage nautical pieces, like a brass telescope or a ship’s wheel for an extra touch of sophistication.Definition - What Defines Preppy?
Preppy
noun: a student or alumni of an expensive college preparatory school or a person resembling such a student in style, dress, and appearance.
adjective: of or characteristic of a student or alumni of an expensive preparatory school, especially with reference to their style of clothing, which is neat, understated, and of high quality, suggesting the wearer is well-off, upper class, and conservative.
According to Urban Dictionary, Preppies are a social class of people who go to preparatory high schools (Groton, Hotchkiss, Philips Exeter, Philips Andover, Deerfield, Laurence, etc.). Most of them shop at J. Crew, Banana Republic, Brooks Brothers, L.L. Bean, Ralph Lauren, and all designer stores.
The Preppy aesthetic has several related aesthetics that are closely associated with it. Overall, these related aesthetics within the Preppy style draw on different historical, cultural, and regional influences to create distinctive looks that are popular among many young people today.
Aesthetics Related to New England or East Coast Prep
Northern Ivy League Preppy style is perhaps the most iconic and classic version of Prep. Originating in the Ivy League colleges and universities of the Northeast, the style is based on clothing worn by college students beginning in the 1940s to about the 1960s. Characterized by tailored blazers, sport coats, suits, oxford shirts, khaki pants, penny loafers, and cable-knit sweaters, Ivy style emphasizes a clean-cut, well-groomed appearance.
A conservative color palette that includes navy, gray, khaki, and brown is paired with natural materials like wool, cotton, and leather. Over time, this style has evolved to include brighter colors, bolder patterns, and more relaxed fits, but the core elements of the look have remained relatively consistent.
Maritime Prep is focused on nautical and sailing elements and includes boat shoes, navy blazers, Breton stripes, and anchor motifs. It is heavily inspired by the sailing culture in New England.
Aesthetics Related to Southern Prep
Other Prep-Influenced Aesthetics
Over the years, the preppy style has also been incorporated into other subcultures, such as punk or grunge. In these subcultures, preppy fashion was often subverted and given an edgier twist.
For example, punk rockers in the 1970s and 1980s might have worn preppy staples like blazers and loafers but paired them with ripped jeans and leather jackets to create a rebellious, anti-establishment look. Similarly, grunge fashion in the 1990s often incorporated elements of preppy style, such as flannel shirts and Doc Martens, but paired them with ripped jeans and unkempt hair to create a disheveled, alternative look.
Today’s preppy fashion enthusiasts embrace a wide range of styles and influences, from classic prep to modern twists on preppy staples. Whether you prefer a preppy blazer and chinos or a preppy-inspired dress with playful prints, there’s no wrong way to rock preppy aesthetic!
Preppy Politics
Though the Preppy aesthetic is not inherently political, it is undeniable that the cultural and historical background of those who subscribe to the aesthetic has influenced their political beliefs and attitudes.
Preppy culture is associated with the WASP culture, which has a long history of political influence in the United States. The WASP culture has often been associated with conservatism and Republicanism, and many Preps have adopted these political leanings.
However, it is important to note that not all Preps align with conservative or Republican beliefs. The Preppy culture is not monolithic, and there are many variations and subcultures within it. Some Preps are far more liberal and progressive.
Furthermore, it is crucial to recognize that the Preppy aesthetic, as with any cultural trend, is not immune to the influence of societal changes and progress. The younger generation of Preps is far more diverse and inclusive than their predecessors. Many younger Preps have embraced liberalism and are active in social justice movements such as Black Lives Matter and LGBTQ+ rights.
The Preppy aesthetic has also been criticized for perpetuating certain outdated and harmful ideas. The Southern Preppy subculture, in particular, has been accused of upholding ideals associated with slavery, racism, and homophobia. The practice of Plantation Weddings and the culture of the Southern Belle, as mentioned in the text, have been called out for romanticizing a problematic past.
Cultural Significance of Preppy Aesthetic
Preppy style isn’t just about looking good – it’s also about embracing a cultural tradition that celebrates the values of hard work, dedication, and community.
American universities, especially those in the Ivy League, played a significant role in the development of preppy fashion. These universities were known for their dress codes, which required students to wear specific clothing items. The clothing items were often expensive and made of high-quality materials, which became a hallmark of preppy style.
Yale and Harvard were two of the most influential schools in this regard. Yale was particularly known for its “Ivy League Look,” which consisted of a navy blazer, gray flannel trousers, and a striped tie. Harvard, on the other hand, was known for its “preppy” look, which featured penny loafers, polo shirts, and madras shorts.
The Jazz Age, which spanned from the 1920s to the 1930s, was a time of great social change and liberation. The clothing styles of this era were more relaxed and comfortable, reflecting the new attitudes towards fashion and life. This period saw the emergence of new styles, such as the sporty look and the “collegiate” style, which drew inspiration from the clothing worn on college campuses.
The Great Gatsby, a novel by F. Scott Fitzgerald published in 1925, featured characters who were wealthy and fashionable, and their clothing choices reflected this. The characters wore items such as tuxedos, flapper dresses, and fur coats, which were luxurious and extravagant.
In the 1960s, the Kennedy family also played a significant role in popularizing preppy fashion. President John F. Kennedy and his wife, Jacqueline Kennedy, were known for their preppy style and often wore clothing items that became associated with preppy fashion, such as boat shoes, trench coats, and slim-fitting suits.
Benefits of Incorporating Preppy Aesthetic into Your Wardrobe
In addition to being stylish and sophisticated, preppy fashion also offers a range of practical benefits including an emphasis on quality craftsmanship and durability, which means that preppy pieces are built to last and can be worn for years to come.
Additionally, preppy clothes are timeless, comfortable, and versatile making pieces easy to dress up or down for any occasion.
Best Preppy Aesthetic Fashion Inspiration
#1 Blair Waldorf Gossip Girl
Blair Waldorf, from the original “Gossip Girl” TV show is the perfect Y2K example of the preppy aesthetic.
Blaire’s wardrobe consists of classic pieces, such as silk headbands, tailored blazers, A-line skirts, and knee-high socks.
Blair’s outfits often feature a refined and understated color palette, with a particular emphasis on navy, white, and pastels.
She frequently wears preppy accessories, like pearl necklaces, brooches, and classic leather handbags.
Beyond her wardrobe, Blair’s personality and behavior align with preppy values of sophistication, propriety, elitism, and academic achievement. Her privileged upbringing and Ivy League education further reinforce her status as a quintessential preppy character.
#2 Cher & Dion from Clueless 1995
Cher and Dion from the movie “Clueless” have a unique 90s fashion take on the preppy aesthetic.
Their fun, youthful preppy outfits feature plaid skirts, knee-high socks, and fitted blazers, all of which are popular preppy staples.
Cher and Dion’s take on preppy style also incorporates a lot of trendy elements, such as crop tops, miniskirts, and colorful accessories.
Mixing preppy pieces with more whimsical items allows them to create a look that is both sophisticated and playful.
Their outfits are often characterized by bold colors, such as pink and yellow, and they frequently experiment with patterns, such as tartan and houndstooth, which add a touch of quirkiness to their preppy ensembles.
Clueless fashion has had a lasting impact on pop culture and has inspired many to embrace a more playful and personalized take on the preppy look.
Chanel’s Spring/Summer 1995 Collection
Chanel’s Spring/Summer 1995 collection, also known as the “New Age” collection, was designed by Karl Lagerfeld and showcased a range of preppy, schoolgirl-inspired looks that were popularized by the 1995 film “Clueless.” The collection featured a mix of classic Chanel designs, such as tweed blazers and skirt suits, with more youthful and playful elements like mini skirts, crop tops, and bright, bold prints.
Some of the standout looks from the collection include a pink tweed skirt suit worn with a matching headband and knee-high socks, a plaid blazer paired with a yellow crop top and matching skirt, and a colorful, graphic-printed dress with a sheer overlay.
The collection was well-received by fashion critics and helped to cement Chanel’s reputation as a trendsetter in the fashion world. Today, the “Clueless” style continues to be a popular fashion trend, with many designers drawing inspiration from the iconic looks of the 1990s.
- Ralph Lauren: Known for its iconic polo shirts, Ralph Lauren’s Polo line is a defining element of preppy fashion, offering a wide range of preppy clothing and accessories, including blazers, cable-knit sweaters, chinos, loafers, and boat shoes.
- Vineyard Vines: A brand that was originally inspired by life on Martha’s Vineyard, Vineyard Vines offers preppy clothing and accessories for both men and women, including bright-colored ties, patterned shorts, and whimsical graphic tees.
- J.Crew: J.Crew is a classic American brand that offers preppy clothing and accessories for men, women, and children. J.Crew became a go-to brand for preppy fashion in the 1990s and 2000s. The brand offered classic preppy staples such as striped shirts, blazers, and khaki pants, along with preppy accessories like boat shoes and canvas tote bags.
- Brooks Brothers: Brooks Brothers, one of the oldest preppy fashion brands in the United States, is a classic American clothing brand that has been associated with preppy style since its founding in 1818. The brand is known for its classic preppy styles, such as button-down shirts, blazers, tweed jackets, and suits.
- L.L. Bean: L.L. Bean is a classic American brand that offers preppy clothing and accessories for men, women, and children. The brand is known for its iconic Bean duck Boots and canvas tote bags, as well as its classic preppy styles, such as cable-knit sweaters and flannel shirts.
- Tommy Hilfiger: Tommy Hilfiger is a preppy fashion brand that offers clothing and accessories for men, women, and children. The brand is known for its iconic red, white, and blue logo, as well as its preppy staples, such as polo shirts and chinos.
- J.Press: J.Press is a traditional American brand that has been associated with preppy style since the 1920s. The brand is known for its tweed blazers, corduroy pants, and classic button-down shirts.
- Sperry: Sperry is a footwear brand that is popular among preppy fashion enthusiasts and has been associated with the style since the 1930s when it introduced the iconic boat shoe that became a staple of summer Prep.
- Lilly Pulitzer: Lilly Pulitzer is a preppy fashion brand that is known for its colorful and whimsical prints. The brand offers preppy dresses, skirts, and accessories that are perfect for a beachy or resort-inspired look.
- Lacoste: Lacoste is a preppy fashion brand that is known for its iconic crocodile logo. The brand offers preppy staples such as polo shirts, sweaters, and tennis skirts.
- Burberry: Burberry is a British fashion brand that is popular among preppy fashion enthusiasts. The brand is known for its classic trench coats, plaid patterns, and preppy staples such as blazers and button-down shirts.
- Tory Burch: Tory Burch is another popular preppy aesthetic fashion brand that offers clothing, accessories, and footwear for women. The brand is known for its signature ballet flats, as well as its preppy styles such as blouses, dresses, and handbags. Tory Burch’s designs often feature classic prints and patterns, such as stripes, polka dots, and florals, and the brand’s logo is a graphic “T” that is often prominently displayed on its products. Tory Burch is a favorite among preppy fashion enthusiasts who appreciate its sophisticated and feminine aesthetic.
- Nautica: Nautica was a brand that became popular in the 1980s for its preppy take on nautical-inspired clothing styles. The brand offered clothing such as striped shirts, windbreakers, and sailor pants, all in classic preppy color schemes like navy blue, red, and white.
- Van Heusen: Van Heusen is a brand that has been around since the early 20th century and is known for its dressier, more formal styles that are also popular in preppy fashion. Their clothing is often characterized by crisp collared button-down shirts, blazers, and khaki pants.
- The Philadelphia Story (1940) – This classic romantic comedy stars Katharine Hepburn as a wealthy socialite whose impending marriage is complicated by the arrival of her ex-husband (Cary Grant) and a tabloid reporter (James Stewart). The movie features elegant costumes, a luxurious mansion setting, and witty dialogue, all of which embody the preppy aesthetic.
- Breakfast At Tiffany’s (1961) – This classic movie follows the story of Holly Golightly (played by Audrey Hepburn), a stylish socialite in New York City who becomes involved with her neighbor. The film is renowned for its fashion, with Hepburn’s iconic little black dress and pearl necklace becoming some of the most recognizable looks in movie history. The setting, characters, and wardrobe all contribute to a preppy aesthetic.
- Love Story (1970) – This romantic drama follows the story of a wealthy Harvard Law student who falls in love with a music student from Radcliffe College. The film showcases the preppy aesthetic with its portrayal of Ivy League colleges, New England scenery, and the characters’ wardrobe of blazers, plaid skirts, and turtlenecks.
- The Great Gatsby (1974) – This film adaptation of F. Scott Fitzgerald’s classic novel is set in the 1920s and follows the story of wealthy Jay Gatsby (played by Robert Redford) and his obsession with a woman from his past, Daisy Buchanan (played by Mia Farrow). The movie features opulent parties, luxurious mansions, and stylish flapper dresses, all of which contribute to its preppy aesthetic.
- Love and Death (1975) – This comedy film is a parody of Russian literature and follows the misadventures of a cowardly Russian soldier during the Napoleonic Wars. The film showcases the preppy aesthetic with its portrayal of the characters’ military uniforms, tailored suits, and formal wear.
- The Facts of Life (1979-1988) – This popular TV sitcom revolves around the lives of a group of girls attending an elite boarding school in upstate New York. The show’s preppy aesthetic is reflected in the characters’ wardrobe of school uniforms, colorful blouses, and pleated skirts.
- Caddyshack (1980) – This comedy follows the hijinks of the members of an exclusive golf club and their interactions with the working-class caddies. Despite the comedic tone, the movie portrays the preppy world of golf clubs, with its strict dress codes, leisurely pace of play, and competitive atmosphere.
- Silver Spoons (1982-1987) – This television series follows a wealthy, teenage boy (played by Ricky Schroder) who moves in with his estranged father and attends a private school. The characters dress in preppy clothing, including blazers, polo shirts, and loafers.
- Class (1983) – This comedy-drama film revolves around the relationship between a wealthy college student and his roommate, a scholarship student from a blue-collar background. The film captures the preppy aesthetic of the Ivy League college culture with its portrayal of the characters’ wardrobe of blazers, khakis, and loafers.
- Trading Places (1983) – This comedy film features a wager between two wealthy businessmen who decide to swap the lives of a wealthy stockbroker and a poor street hustler. The film showcases the preppy aesthetic with its depiction of the Wall Street culture, the characters’ business attire, and the luxurious settings of their social events.
- Making the Grade (1984) – This comedy follows the story of a streetwise delinquent who poses as a prep school student in order to win a bet. The movie explores the culture clash between the street-smart protagonist and the privileged students at the prep school, with the latter’s preppy style and elitist attitudes on full display.
- Sixteen Candles (1984) – This classic coming-of-age movie features a high school student named Samantha who experiences a series of mishaps on her 16th birthday. The film captures the preppy aesthetic of the 1980s with its portrayal of the wealthy and popular kids at school, their designer clothes, and preppy hairstyles.
- St. Elmo’s Fire (1985) – This movie follows a group of recent college graduates as they navigate their way through post-collegiate life. Set against a backdrop of Georgetown University and Washington, D.C., the characters dress in preppy clothing and attend fancy parties, all while dealing with the challenges of adulthood.
- Dead Poets Society (1989) – This drama film follows an English teacher who inspires his students to think for themselves and pursue their passions. The film captures the preppy aesthetic of the elite boarding school with its portrayal of the students’ dress code of blazers, ties, and loafers, as well as the traditional school events such as the poetry recitation competition.
- Beverly Hills, 90210 (1990-2000) – This popular television series follows a group of affluent teenagers living in Beverly Hills, California. The characters attend high school and later college, and their wardrobes consist of preppy staples like polo shirts, blazers, and loafers. The show’s focus on wealth and privilege makes it a classic example of the preppy aesthetic.
- Metropolitan (1990) – This independent film follows a group of young New York socialites as they attend debutante balls and engage in witty conversations. The film captures the preppy aesthetic of the upper-class social scene with its portrayal of elegant mansions, designer clothes, and the characters’ Ivy League education.
- The Bonfire of the Vanities (1990) – This drama film follows a wealthy bond trader who gets involved in a hit-and-run accident in the Bronx. The film captures the preppy aesthetic of Wall Street with its portrayal of the characters’ business attire, luxurious apartments, and country club scenes.
- School Ties (1992) – This drama film follows a Jewish student who receives a scholarship to attend a prestigious prep school in New England. The film captures the preppy aesthetic of Ivy League education with its portrayal of the characters’ wardrobe of blazers, ties, and khakis.
- Scent of a Woman (1992) – This drama follows a young prep school student (played by Chris O’Donnell) who is tasked with looking after a blind, retired Army colonel (played by Al Pacino) over Thanksgiving weekend. The film features a number of preppy clothing staples, including tweed blazers, turtlenecks, and loafers.
- Clueless (1995) – This iconic teen movie follows wealthy high school student Cher (played by Alicia Silverstone) as she navigates her way through Beverly Hills, matching outfits with her best friend Dionne (played by Stacey Dash) and falling in love with her ex-stepbrother Josh (played by Paul Rudd). The movie’s fashion, which includes plaid skirts, knee-high socks, and matching sets, is a quintessential example of the preppy aesthetic.
- White Squall (1996) – This adventure film follows a group of teenage boys who embark on a sailing trip with their captain, played by Jeff Bridges. The film captures the preppy aesthetic of the 1960s with its portrayal of the characters’ wardrobe of polo shirts, khakis, and boat shoes.
- Rushmore (1998) – Directed by Wes Anderson, this comedy-drama tells the story of a precocious student (played by Jason Schwartzman) and his friendship with a wealthy industrialist (played by Bill Murray). Set at a prestigious prep school, the movie features a range of preppy clothing, including blazers, oxford shirts, and khaki pants.
- The Talented Mr. Ripley (1999) – Based on Patricia Highsmith’s novel, this psychological thriller stars Matt Damon as Tom Ripley, a con artist who assumes the identity of a wealthy playboy. Set in 1950s Italy, the film features a range of preppy clothing, including striped blazers, boat shoes, and polo shirts.
- American Psycho (2000) – Based on Bret Easton Ellis’ novel, this film stars Christian Bale as Patrick Bateman, a wealthy investment banker in 1980s New York who leads a secret life as a serial killer. The movie features a range of preppy clothing, including pinstripe suits, power ties, and loafers.
- Legally Blonde (2001) – A comedy about a sorority girl who attends Harvard Law School to win back her ex-boyfriend. It is preppy because it features a protagonist who is fashionable, bubbly, and comes from a wealthy background, which contrasts with the serious and competitive environment of law school.
- The Royal Tenenbaums (2001) – This quirky film from director Wes Anderson tells the story of the dysfunctional Tenenbaum family, who live in a stylish New York City brownstone. The characters’ wardrobes consist of preppy staples like tracksuits, polo shirts, and tweed blazers, and the movie’s overall aesthetic is a mix of vintage and preppy styles.
- The Rules of Attraction (2002) – Directed by Roger Avary, this film is based on Bret Easton Ellis’ novel and follows a group of college students as they navigate relationships and drug use. The movie features a range of preppy clothing, including button-down shirts, cardigans, and blazers.
- Igby Goes Down (2002) – This dark comedy follows the story of a rebellious teenager from a wealthy New York City family who rebels against the constraints of his privileged upbringing. The movie explores the preppy world of the elite Upper East Side, with its extravagant parties, exclusive clubs, and dysfunctional families.
- Gossip Girl (2007-2012) – Based on the book series of the same name, this television show follows a group of wealthy teenagers attending elite private schools in New York City. The characters dress in preppy clothing, including blazers, headbands, and designer handbags.
- Royal Pains (2009-2016) – TV show that follows a doctor, played by Mark Feuerstein, who becomes a concierge doctor for the wealthy residents of the Hamptons. The show is preppy because it takes place in the world of the wealthy elite, with many of the characters dressed in preppy clothing styles such as blazers, collared shirts, and loafers. The show also showcases the preppy culture of the Hamptons, with its lavish parties and social events.
- Hart of Dixie (2011-2015) – A TV show that follows a young New York City doctor who moves to a small town in Alabama to take over her father’s medical practice. The show is preppy because it takes place in the South and features many preppy fashion styles such as sundresses, skirts, and button-down shirts. The show also showcases the preppy culture of Southern hospitality and social events such as debutante balls.
- Moonrise Kingdom (2012) – This quirky coming-of-age story follows the romance between two 12-year-olds who run away together on a New England island in the 1960s. The movie features a nostalgic, preppy aesthetic, with its vintage costumes, pastoral settings, and idyllic summer camp vibe.
- So Undercover (2012): So Undercover is a comedy film that follows a tough, street-smart private investigator, played by Miley Cyrus, who is recruited by the FBI to go undercover at a college sorority. The film is preppy because it takes place in the world of college Greek life, with many of the characters dressed in preppy clothing styles such as collared shirts, sweaters, and skirts.
- Southern Charm (2013-) – Reality television series that follows the lives of wealthy socialites living in Charleston, South Carolina. The show features a preppy aesthetic with its focus on the characters’ fashion choices, which often include brightly colored Lilly Pulitzer dresses and preppy polo shirts, and their lavish lifestyles. The show also highlights the social hierarchies and class divides that are often present in preppy circles, as well as the characters’ struggles to balance their personal lives with their public personas.
- Annabelle Hooper and the Ghosts of Nantucket (2016) – A family-friendly adventure film about a teenage mystery writer who solves a ghostly mystery on the island of Nantucket. It is preppy because it takes place in a picturesque and affluent vacation destination, where the characters wear preppy clothing and enjoy outdoor activities like sailing.
- Hidden Figures (2016): This is a biographical drama film about three African American women who played key roles in the early years of NASA’s space program. It is not typically considered a preppy film, as it focuses on the serious themes of racial and gender inequality, but it does include scenes that depict the fashion and style of the early 1960s, which could be considered preppy.
- Filthy Preppy Teens (2017) – A satirical TV show that follows a group of wealthy and privileged high school students as they navigate the social hierarchy of their elite private school. It is preppy because it highlights the excesses and extravagance of the wealthy elite, and the social codes and expectations that come with being part of this exclusive world.
- The Marvelous Mrs. Maisel (2017 -) – TV series that follows a housewife, played by Rachel Brosnahan, who becomes a stand-up comedian in the 1950s. The show is preppy because it takes place in the world of upper-class New York City, with many of the characters dressed in preppy clothing styles such as dresses, skirts, and blouses. The show also showcases the preppy culture of the time, with its emphasis on social events, etiquette, and style.
- Knives Out (2019): A modern murder mystery film that follows the investigation into the death of a wealthy patriarch, played by Christopher Plummer. The film is set in a luxurious mansion, and the characters are all part of a wealthy, upper-class family. The film is preppy because it showcases the luxurious lifestyle of the wealthy family, with many of the characters dressed in preppy clothing styles such as blazers, collared shirts, and loafers.
- The Politician (2019-) – A satirical comedy-drama series that follows the life of wealthy high school student Payton Hobart (Ben Platt) as he runs for student body president with the ultimate goal of becoming President of the United States. The show’s preppy aesthetic is apparent in its characters’ wardrobe choices, which often feature classic pieces like blazers, polo shirts, and pearls, and in the Ivy League schools that they attend. The show’s themes of ambition, privilege, and political maneuvering also fit well with the preppy genre.
- Emma (2020) – A period comedy-drama film based on Jane Austen’s novel of the same name. It is preppy because it showcases the lives of the wealthy gentry of Regency England and their preoccupations with social status, fashion, and courtship.
- The Sex Lives of College Girls (2021-) – comedy series that follows four college roommates as they navigate the ups and downs of college life. The show features a preppy aesthetic with its characters’ wardrobe choices, which often include plaid skirts, polo shirts, and oversized cardigans, and in the characters’ Ivy League college setting. The show also explores themes of class and privilege, as well as the pressures that come with attending a prestigious university.
Sports
- Badminton: The perfect sport for those who like to look fancy while still getting some exercise. Plus, who doesn’t love the sound of a shuttlecock being smacked around?
- Bocce ball: A classic lawn game that’s all about precision and strategy. It’s like bowling, but with more sunshine and fewer rental shoes.
- Pool: Whether you’re a pro hustler or just like to play around with a few friends, there’s nothing like a game of pool to make you feel like you’re living the high life. Hanging out at the pool in a sporty bikini is also acc
- Croquet: The ultimate preppy sport, played with mallets and balls on a pristine lawn. Whacking your opponents with mallets in the spirit of competition is considered bad manners.
- Fencing: Channel your inner musketeer with this elegant and precise sport. En garde!
- Golf: A game of skill, strategy, and patience. And if you’re lucky, you might even get to drive around in a fancy little golf cart.
- Lacrosse: The official sport of preppy high school jocks everywhere. Just make sure to stock up on spare sticks as they tend to break at the most inconvenient times.
- Polo: Both on water and on horseback, polo is the sport of kings (and those who aspire to be). Remember your helmet and your trusty steed!
- Rowing: There’s nothing quite like gliding across the water in a sleek, carbon-fiber single scull. If you’re lucky, you might even get to wear a blazer with a fancy crest on it.
- Sailing: For those who prefer wind power over oars, sailing is the ultimate preppy water sport. Bring your boat shoes!
- Skiing: Hit the slopes with this stylish winter sport. Pack your après-ski Japanese fox fur sweater and your hot cocoa thermos.
- Squash: A fast-paced and intense racquet sport that’s perfect for those who like to work up a sweat under their Ralph Lauren Polo. Try not to hit your opponent in the face.
- Tennis: A preppy classic, played in doubles with a can of balls.
Social Activities
- Wine tastings: Wine tastings are a sophisticated and social activity that many preppy individuals enjoy. Whether you’re a wine connoisseur or just enjoy trying new things, a wine tasting event can be a fun way to socialize.
- Sailing: Sailing is a popular preppy activity that can be enjoyed with friends and family. Many preppy individuals enjoy taking their boats out on the water and participating in regattas.
- Polo: Polo is a sport that is often associated with preppy culture, but it’s also a great social activity. Many preppy individuals enjoy watching polo matches and socializing with other attendees.
- Golf: Golf is a classic preppy sport, but it’s also a great way to socialize with friends and colleagues. Many preppy individuals enjoy playing golf together and then enjoying drinks or a meal afterwards.
- Charity events: Preppy individuals are often involved in charitable causes and fundraising events. Attending a charity gala or auction can be a great way to socialize while supporting a good cause.
- Art shows and museum exhibits: Many preppy individuals appreciate art and culture, and attending art shows and museum exhibits can be a great way to socialize and expand your knowledge.
- Concerts and music festivals: Preppy individuals often have a love for music, and attending concerts and music festivals can be a fun way to socialize with friends and enjoy live performances.
- Book clubs: Reading and discussing literature is a popular pastime among preppy individuals. Joining a book club can be a great way to meet new people and engage in thoughtful discussions.
- Black tie and cocktail parties: Black tie and cocktail parties are popular preppy social events where attendees dress up in formal attire and socialize over drinks and hors d’oeuvres. These events are often held to celebrate special occasions, such as weddings or charity fundraisers.
- Debutante Balls: These formal events where young women are introduced to society, are often associated with preppy culture and are typically held in the South.
- Vacationing in The Hamptons, Martha’s Vineyard, and Cape Cod: These are popular vacation destinations among preppy individuals. They offer beautiful beaches, quaint towns, and plenty of opportunities for outdoor activities such as sailing, golfing, and tennis.
- The Kentucky Derby: The Kentucky Derby is an annual horse race held in Louisville, Kentucky. It’s a popular event among preppy individuals who enjoy dressing up in their finest attire and socializing with friends while watching the race.
- Yachting: Yachting is a popular preppy activity that involves sailing on a yacht. Many preppy individuals enjoy taking their boats out on the water and participating in regattas.
- Tennis: a classic preppy sport that is often played in country clubs and other upscale settings. Many preppy individuals enjoy playing tennis as a way to socialize with friends and get exercise.
- Needlepoint: a preppy pastime that involves stitching designs onto canvas using a needle and thread. It’s often used to create decorative items such as pillows and belts.
- Photography: a popular hobby among preppy individuals who enjoy capturing the beauty of nature and the world around them. Many preppy individuals also enjoy collecting vintage cameras and photography books.
Whites
Wearing whites is mission critical, wearing dingy, dated whites is unacceptable.
Douchiness
Preppy clothing poses the danger of appearing extremely douchy so take care not to give off this vibe.
Prep is a colloquial term that refers to a type of private school education in the United States. These schools are often called “prep schools,” “preparatory schools,” or “boarding schools” and they typically serve students from grades 9 to 12 (ages 14 to 18).
The primary goal of these schools is to prepare students for admission to highly selective colleges and universities. They offer a rigorous academic curriculum and often have a strong emphasis on extracurricular activities such as sports, music, and theater.
Prep schools are known for their highly competitive admissions processes, and they often require applicants to demonstrate exceptional academic and extracurricular achievements. The cost of tuition at prep schools is generally high, and they are often attended by students from affluent families.
The culture and lifestyle associated with prep schools and their graduates is often referred to as “preppy.” This lifestyle is characterized by a particular fashion style, as well as a set of values and social practices that are associated with affluence, education, and social status.
- Polo shirts and button-down
- Oxford shirts
- Sweaters and cardigans
- Khaki or chino pants
- Skirts and dresses in classic patterns like plaid, houndstooth, and argyle
- Loafers, boat shoes, and other classic footwear
- Blazers and sport coats
- Accessories like scarves, belts, and hats
The Official Preppy Handbook
The Official Preppy Handbook is a humor book written by Lisa Birnbach that was first published in 1980. It satirizes and celebrates the culture of prep schools and upper-class America, as well as the fashion, customs, and values associated with this lifestyle.
The book covers a wide range of topics, including the history of preppy culture, preppy fashion (such as Lacoste shirts and Bass Weejun loafers), preppy hobbies (such as sailing and tennis), and even preppy pets (such as English Springer Spaniels). It also includes tongue-in-cheek quizzes, such as “Are You Preppy?” and “What Kind of Preppy Are You?”
The Official Preppy Handbook was a cultural phenomenon that sold over a million copies and spent several months on the New York Times bestseller list.
Some of the preppy fashion trends popularized by the book include polo shirts, khaki pants, Sperry Top-Sider boat shoes, and the “preppy” haircut (short on the sides, longer on top).
One of the most enduring legacies of The Official Preppy Handbook is the term “preppy” itself. Prior to its publication, the term “preppy” was mostly used to describe students who attended prep schools. But Birnbach broadened the definition to include anyone who embraced the preppy lifestyle, regardless of their educational background.
Movies and TV shows like “The Gilmore Girls” and “Clueless,” have even referenced the book on screen. Birnbach herself went on to write several other books, including a sequel to “The Official Preppy Handbook” called “True Prep.”
Sources / Citations
Lingala, A. (2013). The Origin and Evolution of Prep and its Socioeconomic Relevance.
Risinger, C. R. (2016). The Unofficial Preppy Uniform: Yesterday, Today, and Tomorrow (Doctoral dissertation, Kent State University).
Kim, J. Y. (2015). Analysis of the preppy look design as shown in the domestic men’s wear collection. The Research Journal of the Costume Culture, 23(6), 987-1003.
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