The movies that defined 90s and 2000s fashion
Step back in time to the era of iconic style and unforgettable looks. These films didn't just tell stories; they dictated trends and influenced wardrobes for a generation.



Movies have always been a powerful mirror and shaper of culture, and the late 20th and early 21st centuries saw cinema play a massive role in defining fashion. From the hallways of high school to the bustling streets of New York City, certain films became instant style bibles.
Think about the lasting impact of Patricia Field's costume design, not just on TV's Sex and the City, but also its big-screen adaptation and films like The Devil Wears Prada. Her work wasn't just about clothes; it was about using fashion as a narrative tool, showcasing transformation and personality.
Beyond the high-fashion world, films like Clueless created a preppy, plaid-filled aesthetic that remains instantly recognizable and frequently referenced today. It captured a specific moment in 90s teen culture, where style was a crucial part of identity and social hierarchy.
These movies often featured characters undergoing significant personal growth, with their evolving style mirroring their journey. Whether it was Mia Thermopolis finding her royal grace in The Princess Diaries or Andy Sachs navigating the cutthroat fashion industry, the visual transformation was as key as the plot points.
They reminded us that fashion can be fun, aspirational, and sometimes, deliberately quirky. While some outfits might now look like charming period pieces, others remain timeless inspirations, proving that cinematic style can have a long shelf life.
14. The Proposal (2009)
The Proposal is a delightful romantic comedy starring Sandra Bullock as a high-powered book editor facing deportation to Canada. To avoid this, she convinces her young assistant (Ryan Reynolds) to marry her. The film's focus is primarily on the comedic premise and the developing relationship between the two leads as they pretend to be a couple while visiting his quirky family in Alaska. While Bullock's character has a sophisticated, put-together style that contrasts with the more casual setting, fashion isn't a central theme, making it a fun watch for the chemistry and laughs.

13. The Sisterhood of the Traveling Pants (2005)
The Sisterhood of the Traveling Pants is a heartwarming story about four best friends who are separated for the summer but stay connected through a magical pair of jeans that seemingly fits them all perfectly despite their different body types. The film focuses more on the emotional journeys and experiences of the four friends as they navigate love, family, and self-discovery. The pants themselves are a symbol of their bond and the idea that true connection transcends physical appearance, making it a touching tale about friendship.

12. Crazy, Stupid, Love. (2011)
Crazy, Stupid, Love. is a multi-layered romantic comedy with a great ensemble cast. One of the film's key subplots involves Ryan Gosling's character, Jacob, giving a style makeover to Steve Carell's character, Cal, after Cal's wife asks for a divorce. This transformation highlights how changing one's appearance can boost confidence and change how others perceive you. While not solely focused on fashion, the style aspect is a significant and amusing part of the story, contributing to the film's exploration of love and reinvention.

11. Bridget Jones's Diary (2001)
Bridget Jones's Diary, based on the hit novel, stars Renée Zellweger as Bridget, a single British woman in her early thirties navigating her career, love life, and self-improvement goals. Bridget is incredibly relatable in her struggles with dieting, smoking, and finding the right partner. Her style is often more about comfort and reality than high fashion, famously including the moment she wears large control briefs. It's a charmingly awkward and hilarious romantic comedy that resonates with anyone who's ever felt a bit imperfect while trying to figure things out.

10. The Princess Diaries (2001)
The Princess Diaries tells the story of Mia Thermopolis (Anne Hathaway), an awkward San Francisco teenager who discovers she is the heir to the throne of Genovia. This revelation leads to a significant transformation, both internally and externally, including a major style and beauty makeover guided by her grandmother, Queen Clarisse Renaldi (Julie Andrews). The film is a sweet and funny coming-of-age story about embracing your true self and destiny, with the physical transformation serving as a visual representation of Mia stepping into her new role.

9. How to Lose a Guy in 10 Days (2003)
How to Lose a Guy in 10 Days is a fun and clever romantic comedy starring Kate Hudson as Andie Anderson, a magazine journalist writing an article about, you guessed it, how to lose a guy in 10 days. Matthew McConaughey plays the ad executive who has bet he can make any woman fall in love with him in the same timeframe. Andie's job at a fashion/lifestyle magazine means style is part of her world, and her attempts to be the most annoying girlfriend ever involve some memorable outfits and antics. It's a charming battle of the sexes with great comedic timing.

8. The Intern (2015)
The Intern features Anne Hathaway as Jules Ostin, the founder of a successful online fashion retailer, who agrees to take on a 70-year-old widower (Robert De Niro) as her intern. While not solely focused on high fashion, the film is set within the world of e-commerce style and contrasts the modern, fast-paced environment of Jules's company with the old-school charm and wisdom of De Niro's character, Ben. It's a heartwarming story about intergenerational friendship, adapting to change, and balancing work and life, with the fashion industry setting providing a stylish backdrop.

7. Mean Girls (2004)
Mean Girls is a sharp, hilarious look at the social hierarchy of high school, written by Tina Fey. Lindsay Lohan plays Cady Heron, a homeschooled teenager who suddenly finds herself navigating the complex world of cliques, including the infamous 'Plastics'. The film brilliantly uses clothing and appearance as a way to define social groups and conformity. From the Plastics' strict dress code ('On Wednesdays we wear pink!') to Cady's attempts to fit in, style is integral to the movie's social commentary. It's a witty and enduring comedy that perfectly captures the absurdity of high school dynamics.

6. Pretty Woman (1990)
A modern fairy tale, Pretty Woman is a classic romantic comedy that launched Julia Roberts into superstardom. She plays Vivian Ward, a street-smart woman whose life changes dramatically after meeting wealthy businessman Edward Lewis (Richard Gere). The film is famous for its Cinderella-esque transformation arc, most notably seen in Vivian's style evolution from her initial look to elegant gowns. The shopping montage on Rodeo Drive is particularly iconic. It's a charming, feel-good story with great chemistry between the leads and a truly unforgettable soundtrack.

5. Confessions of a Shopaholic (2009)
Confessions of a Shopaholic stars the delightful Isla Fisher as Rebecca Bloomwood, a young woman with a serious shopping addiction who lands a job writing for a financial magazine ironically giving advice on saving money. The film, also featuring costumes by Patricia Field, leans heavily into the visual appeal of fashion and shopping, depicting Rebecca's overwhelming desire for material possessions. It's a lighthearted romantic comedy that explores the consequences of consumerism through a charming but flawed protagonist, offering plenty of stylish eye candy along the way.

4. Sex and the City (2008)
Taking the beloved TV series to the big screen, the Sex and the City movie continues the fashion-forward adventures of Carrie, Samantha, Charlotte, and Miranda in New York City. Fashion remains a central character, with Patricia Field once again crafting iconic looks that reflect each woman's personality and journey. The film delves deeper into the characters' relationships, tackling themes of marriage, motherhood, and self-discovery in their late 30s and 40s. It's a glamorous, emotional extension of the show that fans adored, filled with designer labels and heartfelt moments.

3. Legally Blonde (2001)
Legally Blonde is pure joy and empowerment! Reese Witherspoon shines as Elle Woods, a fashion-loving sorority girl who decides to follow her ex-boyfriend to Harvard Law School. Don't let the pink wardrobe fool you – Elle is incredibly intelligent and determined, constantly defying stereotypes and proving everyone wrong. The film cleverly uses Elle's distinctive style not just as a visual gag, but as an integral part of her identity and confidence. It's a genuinely feel-good movie about staying true to yourself, overcoming prejudice, and succeeding on your own terms, all delivered with wit and charm.

2. Clueless (1995)
Clueless is a total classic and a definitive style icon of the 90s! Alicia Silverstone is utterly charming as Cher Horowitz, a wealthy Beverly Hills teenager navigating high school, friendships, and makeovers. The film's fashion, curated by costume designer Mona May, is instantly recognizable and influential, from Cher's yellow plaid suit to Dionne's oversized hats. Beyond the iconic looks, the movie is a smart, witty adaptation of Jane Austen's 'Emma', offering sharp social commentary on youth culture and privilege. It's endlessly rewatchable, laugh-out-loud funny, and its unique slang even influenced a generation.

1. The Devil Wears Prada (2006)
The Devil Wears Prada is an absolute must-watch, taking you deep into the high-stakes, often ruthless world of fashion magazines! Meryl Streep delivers an absolutely pitch-perfect performance as Miranda Priestly, the demanding editor-in-chief who is both terrifying and fascinating. Anne Hathaway is fantastic as Andy Sachs, the ambitious but naive assistant trying to survive Miranda's impossible requests. The costume design by Patricia Field, known for her work on 'Sex and the City', is simply breathtaking, showcasing incredible designer pieces that practically make the movie a runway show itself. It's a brilliant look at ambition, sacrifice, and finding your own path, all wrapped up in a ridiculously stylish package.
