9 Top Preppy Movies with Timeless Fashion Sense

talented mr ripley preppy outfits
Reading Time: 8 minutes

90sfashion.com is a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for sites to earn advertising fees by advertising and linking to Amazon.com. As an Amazon Associate we earn from qualifying purchases. See our disclosure here.

Last Updated on January 6, 2022

Get ready for the weekend with a binge-worthy ultimate list of preppy films!

They all have fashion that is to-die-for, amazing casts, and terrific plots. And as if that wasn’t enough, scroll down to the very bottom for some bonus TV series that were too amazingly preppy not to be included!

The Chosen:

We have picked top titles of the 80s, a bunch of 90s hit movies, and some recent films that really pulled all the stops in their costume department. Each of these movies has a very unique and personal approach to the preppy fashion style. 

We’ve already talked about what makes preppy style tick here, so check it out if you want all the details of this fashion style. But basically, this means that they use a ton of uniforms in block colors, shields, plaid mini skirts, nautical elements, rugby t-shirts, skinny trousers, pastel chinos, leather loafers, boating shoes, and so on. 

#1 Risky Business (1983)

Key Items:

  • Checkered shirts
  • Striped polo t-shirts
  • Varsity sweatshirts
  • Varsity jackets
  • Grey tweed blazers
  • Ray-Ban Original Wayfarers Sunglasses

When Joel Goodson’s parents go away on a trip, he decides to make the most of it and enjoy his freedom while he is home alone, but things soon spiral out of control.  

It is indeed Risky Business when you are mugged by a lady of the night, her pimp is after you, your father’s Porsche ends up water deep in the pier, and your furniture is burgled the night before your parents return! 

Risky Business was Tom Cruise’s break-out movie and one of its most memorable scenes is one of the most copied lip-sync dances ever. Can you recognize it? It is without a doubt my favorite scene! After all, who hasn’t had a moment like this when no one is around to judge our dance moves? 

What I love about the fashion in this movie is how understated American preppy it is. There are no uniforms or plaids on sight, but the varsity sweatshirts and jackets keep reminding us that this is an Ivy League type of kid and that he is in fact, loaded.

His choice of Ray-Ban Original Wayfarers Sunglasses skyrocketed them to fame and forever positioned the model as 80s cool sunglasses to invest on. 

#2. Making the Grade (1984)

Key Items:

  • Pastel sweaters
  • Pastel skinny trousers
  • Polo shirts
  • Layering shirts/sweaters
  • Grey overcoats
  • Pearl necklaces

A rich prep kid, Palmer Woodrow, finds himself forced to attend a last-chance Academy after a string of expulsions or be forever cut off financially by his currently traveling abroad parents. 

Thankfully for him, he finds con artist Eddie Keaton, who is in dire need of money to pay back what he owes to a local loan shark. One thing leads to another, and Keaton ends up attending prep school in Woodrow’s place, freeing him to take up skiing in Europe and graduating for him.

This is by no means a great film, but it is quite fun if you enjoy light comedy and an unraveling scheme. Plus, the preppy clothing is on point. Woodrow’s signature pink sweater tied over the shoulders and colored skinny pants are a quiet testament to the 80s The Official Preppy Handbook.

There’s also a ton of Argyles sweaters, typical preppy layering of rugby t-shirts with button-down sweatshirts, pastel yellow skinny trousers, and leather loafers.

Read: 90s Style Men’s Sweaters Guide

#3. Dead Poets Society (1989)

Key Items:

  • Argyles sweaters
  • Varsity sweatshirts
  • Corduroy and tweed blazers
  • Striped neckties
  • Striped tan scarves

A group of teens discover their own voice and fight against the status quo at an all-boys boarding school, guided by the unorthodox English teacher John Keating (played by Robin Williams). 

The students find inspiration in poetry to “seize the day” and face the enormous pressure placed upon them by their parents and the school. An absolute must-watch with top performances, amazing dialogues, and a riveting plot!

Although there are many gems in this dialogue-heavy movie, my favorites quotes by John Keating are: 

  • Carpe diem, seize the day. Gather ye rosebuds while ye may” 
  • There’s a time for daring and there’s a time for caution, and a wise man understands which is called for

Fashion-wise, the movie portrays the environment of the school and the suffocating Ivy League expectations perfectly. Students wear identical uniforms with shields, classic cut blazers, and striped neckties while teachers don corduroy jackets, tweed blazers, and printed bowties. It is the perfect New England preppy style, with muted dark colors like olive, gray, and navy.  

#4. Clueless (1995)

Key Items:

  • Oxford shirts
  • Plaid skirts
  • Argyles sweaters
  • Nordic vests
  • Plaid matching sets
  • Kneesocks

Cher is a shallow and rich popular girl at the top of her Beverly Hills high school’s pecking order that is about to fail a course. She believes that her teacher is grading her so harshly because he is unhappy, so she decides to take it upon herself to play matchmaker and make her grades go up.

Her success prompts her to apply her matchmaking skills to her friends and her own life to rather disastrous effects. 

Cher might seem a bit callous at first, but she is soon revealed to be witty, caring, and although clueless, to have a very good heart that shines through in the end. 

Some of my favorite quotes from the movie are:

Josh: Do you have any idea what you’re talking about?

Cher: No. Why, does it sound like I do?

Cher: Do you prefer “fashion victim” or “ensembly challenged”?

Writers actually sat in classes at Beverly Hills High to get the flavor of how the students talked to one another and the whole movie was filmed over a 40-day shooting schedule!

One of the reasons why I am such a Clueless fan is that it made history with its sartorial choices. At a time when teenagers were going for grunge styles, it revived the preppy trend by taking Ivy League key items and creating something that transmitted the preppy kid vibe but felt new and modern. 

Speaking of plaid… In fact, there were 53 different kinds of tartan and plaid used, 7 of which were worn by Cher and 12 by other major characters. There is so much to say about the amazing fashion ensembles that Cher and crew wear that it required its own blog post!

Read: 17 Preppy Outfit Ideas for that Next Outing (Women’s Edition)

#5. Rushmore (1998)

Key Items:

  • Striped necktie
  • Corduroy blazer
  • Tuxedo bow tie
  • Tan chinos

Max Fischer is the king of extracurricular activities. Be it beekeeping or writing and producing plays, there is little he doesn’t do. But he is in fact, failing all of his other classes! 

Things begin to tumble down when he finds out he is on academic probation, falls in love with an elementary school teacher, and befriends an industrialist businessman who is also attracted to the teacher. A love triangle ensues and chaos, and war, soon follow.

Rushmore is one of Wes Anderson’s less-known movies. It is also where he met Bill Murray, whom he worked with on every subsequent film ever since. 

My favorite Max Fischer quote is this little classic gem:

Herman Blume: She’s my Rushmore.

Max Fischer: I know. She was mine too.

There is much to say about the particular flavor of Wes Anderson movie’s general aesthetic, however, what I loved the most about Rushmore was its preppy yet whimsical fashion style that takes elements from the trend and makes them part of its story narrative.

In the case of Max, his excentric personality shines through in his color-blocking blue uniform, red beret hat, and striking velvet green blazer, to the point that each is as much a protagonist as Max himself. 

Read: 24 Preppy Clothing Brands That Have Stood the Test of Time

#6. The Talented Mr. Ripley (1999)

Key Items:

  • Classic Blazers
  • Polo shirts
  • Oxford shirts
  • Button-down sweaters
  • Corduroy Jackets
  • Skinny trousers
  • Colored chinos
  • Cashmere turtlenecks
  • Soft Soled Leather Shoes
  • Loafers
  • Brogues
  • Striped sweaters
  • Striped scarves
  • Nautical everything

Tom Ripley is mistaken for a Princeton graduate at a party and sent to Italy to retrieve Dickie Greenleaf, a rich and spoiled playboy. Soon after, Ripley develops an intense attachment to Dickie and his privileged lifestyle that becomes obsessive and spirals into violence.

The cast provides superb performances for a nuanced and outstanding film. The locations are beautiful and the wardrobe is a Mediterranean dream come true! Can’t recommend it enough!

My favorite quote from the film is this iconic reflection:

Tom Ripley: I always thought it would be better to be a fake somebody than a real nobody.

As is often the case with great movies, a character’s clothing says a lot about them. Ripley’s clothing evolves throughout the film to reflect his innocence, inner turmoil, and personal demons, as well as his need to fit and transform himself. 

Soft top-notch leather loafers, white rolled-back chinos, and subtle nautical ensembles reflect Dickie’s moneyed background, whereas Ripley’s corduroy jacket is made to look haggard next to Dickie’s classic navy jacket. He adopts Dickie’s clothing style little by little as he is consumed by his obsession and begins to transform himself.  

Funny Fact: Dickie’s favorite men’s tailor in Rome, Battistoni, is a real shop in Via Condotti street, founded in 1946. Isn’t that really cool?

Read: What Was Life Really Like in the 1990s?

#7. Cruel Intentions (1999)

Key Items:

  • Oxford shirts
  • Classic navy blazers
  • Sweaters tied around the shoulder
  • V neck striped sweaters
  • Plaid midi skirts

Two spoiled manipulative and wealthy step-siblings (Sarah Michelle Gellar and Ryan Phillippe) of an elite Manhattan prep school conspire by making a wager of sexual conquest regarding naïve Cecile (Selma Blair) and virginal Annette (Reese Witherspoon) before the start of term. Let the games begin!

This classic 90s teen drama was a huge hit back in the day. I remember watching it and boy, did we think it was hot! I was already a huge Sarah Michelle Gellar because of Buffy but this movie really made me like Reese Witherspoon too. It was a few years before Legally Blonde, so she was still a quite unknown woman.

The movie made exemplary use of the power of preppy clothing to depict a teen’s rich and proper persona. Cecile, who is originally very sheltered and naive, is decked in full preppy fashion.

Her mint sweater is loosely tied over her shoulders and her plaid pink skirt reaches her knees, whereas Kathryn (Gellar’s character) dons corsets and dark clothing to further distance her from the pearl-wearing good girls. 

According to Denise Wingate, who was the costume designer, Witherspoon was deliberately clothed in light colors to contrast with the dark colors of Phillippe. 

Fun Fact: Witherspoon and Phillippe were a couple at the time he was cast and the director loved the idea of casting her too, so he begged her to accept the part!

#8. Mona Lisa Smile (2003)

Key Items:

  • Checkered overcoats
  • Tweed blazers
  • Striped scarves
  • Plaid midi skirts
  • Classic sweaters
  • V neck vests
  • Wide lapel shirts
  • Pearl necklaces

Rich preppy girls attending Wellesley’s private liberal arts college are taught art by a free-thinking professor who insists on making them question their traditional social roles. 

It wasn’t uncommon for women in 1950 to go to college to bid their time until they found a husband and it is precisely this reality against which Katherine Ann Watson, played by Julia Roberts, wants her students to rebel so that they can realize their full potential.

One of my favorite quotes from this movie is this very simple line:

Katherine Watson: Look beyond the paint. Let us try to open our minds to a new idea.

Fashion-wise, this movie is a little gem. The trove of amazing sweaters and retro skirts is simply dashing! I would totally welcome many of these clothing items into my wardrobe. A must-watch essential on any preppy list!

#9. The Riot Club (2014)

Key Items:

  • Tuxedo jackets
  • Puffer jackets
  • Plaid neckties
  • V neck sweaters
  • Chino trousers
  • Plaid blazers
  • Leather loafers

Two first-year students attending Oxford University are invited to join the infamous Riot Club. The long-established exclusive drinking club prides itself on its hedonism and on making the most of the privileges that money can buy. The initiation ceremony soon gets out of hand and things escalate, with dire consequences for some of the involved.

This movie raises a lot of moral issues regarding the inequality between different types of people, the immunity that money can buy, and the consequences of one’s actions. Undoubtedly, the depiction of British preppy fashion is this movie’s strongest suit. Not to say it is a bad movie, but it is merely okay. The costumes make it totally worth it though!

Little-known fact: Robert Pattinson was considered for one of the lead roles but in the end, he was not cast. 

Some movies didn’t make the cut because they didn’t have enough of a preppy wardrobe. However, they had a couple of fashionable preppy moments that were totally worth mentioning!

Special Mentions:

#10. Annie Hall (1977)

Ralph Lauren, being the ultimate preppy brand, took care of making Diane Keaton’s wardrobe in Annie Hall a memorable sight. Pairing a masculine black vest with a printed tie, classic white shirt, and tan trousers would forever be a classic after this movie. Let’s not forget the fedora wool hat too!

#11. Legally Blonde (2001)

Reese Witherspoon’s New England preppy ensemble with teal green knit cardigan and plaid purple tie creates a preppy look with a touch of sweetness that totally fits her character.

#12. Gossip Girl (2007)

This TV series is, without a doubt, one of the most recent depictions of Clueless’s style of preppy fashion. Preppy school uniforms are reimagined with a modern twist all throughout the series, but particularly so for Blair Waldorf’s character.

The queen of padded tiaras and plaid blazers dons amazing outfits that play around with the idea of a school uniform gone high fashion and use all the usual suspects of the preppy trend: Argyles sweaters, plaid pleated mini skirts, Mary Janes, knee socks, uniform blazers, and fashionable neckties in many forms.

Read: Outfits with Mary Janes: How to Style Mary Jane Shoes

Previous article24 Preppy Clothing Brands that Ooze Sophistication
Next articleDr. Martens: The Styles and Models that Made History
Lorena Lombardo
Lorena Lombardo is a fashion designer specialized in trend forecasting and fashion journalism. She studied at the UAL (University of London), ORT (Universidad ORT Uruguay), and taken various courses about traditional craftsmanship while living in Tokyo. Some of her favorite memories during the 90s include wearing bucket hats and trying to copy Rachel’s hairstyle. Her absolute favorite show was Buffy: the Vampire Slayer but she was also a huge fan of Clueless because of its amazing fashion choices. Her top track of the decade is currently disputed between How soon is Now? by the Smiths and Here with me by Dido. Both also happen to be the opening songs for two great 90s shows: Charmed and Roswell. Coincidence? I think not!