7 Iconic Movie Makeovers From the '90s and 2000s We Still Can't Stop Talking About

There was a time, a simpler time, when all it took to reinvent yourself was a shopping spree, a new hairstyle, and a motivational soundtrack to pair with five minutes of screen time, which almost always included a grand reveal (in slow motion, naturally).  

Enter: a 90s and 2000s movie makeover montage. 

These iconic before-and-after moments gave birth to the very idea of main character energy, made dresses and heels the catalyst of change, and reminded us all that fashion can, in fact, be used as a storytelling tool. We expected these makeovers to turn the characters' lives around for the better, and sometimes, they did, but not in the way we initially assumed and certainly not without a healthy dose of self-realization.

These style revivals are immortalized in film for how they make the characters feel and what those feelings teach us about life. They basically turned the page on a new chapter of mental clarity and self-discovery that transcended outer beauty, one fabulous ensemble and eyebrow tweeze at a time. 

Let’s press play on the movie makeovers of the 90s and 2000s that became trendsetting forces, and maybe pick up a few lessons about life, love, and self-worth along the way. 

1. Pretty Woman (1990)
2. Clueless (1995)
3. She's All That (1999)
4. Never Been Kissed (1999)
5. Miss Congeniality (2000)
6. The Princess Diaries (2001)
7. The Devil Wears Prada (2006)

Pretty Woman (1990)

The Makeover

Vivian Ward goes from an escort on Hollywood Boulevard to a prestigious guest at the Regent Beverly Wilshire Hotel following a transformation so renowned it became a landmark in cinema. Vivian, played by Julia Roberts, is paid to accompany wealthy business mogul Edward Lewis to a handful of social events, but first, she must look the part. After a few failed attempts to communicate with rude retail associates (big mistake, huge!), she secures a wardrobe that is the epitome of class and brings out her natural charm.

The Result

Though Vivian refreshes her wardrobe and alters her mannerisms to fit into Edward’s world, she never changes who she really is. Her physical evolution gives her the inner confidence to want more for herself and to seek a life that truly suits her.

And just when all hope for romance seems lost, Edward arrives in a limo, bouquet in hand, and climbs the fire escape to sweep Vivian off her feet, proving the real transformation is a change of heart. 

Clueless (1995)

The Makeover

Cher Horowitz rules the school alongside her best friend Dionne Davenport and other notably popular Bronson Alcott students. Deciding to use her influence for good (not sporadically), she helps an offbeat new student, Tai Frasier, blend in with her crowd. Tai gets a new hair color, a wardrobe revamp, and a front-row seat in an elite social circle. 

The Result

This metamorphic glow-up forces both Cher and Tai to confront the compromises popularity demands. As if!

Cher comes to value individuality (especially after being reminded that she is a virgin who can’t drive), which inspires her to find a match for herself. Tai leaves behind her popular alter ego to embrace her authentic self, ultimately finding a more genuine connection with her friends and a skater boy that’s more her speed.  

She's All That (1999)

The Makeover

For millennials, the title She’s All That instantly conjures the image of Laney Boggs (”get your cute butt down here!”) descending the stairs in a red mini dress to “Kiss Me” by Sixpence None the Richer, catching the eye of the most popular boy in school. Zack Siler and Dean Sampson’s infamous bet on Laney (an artsy high school senior with no regard for fitting in) becoming prom queen sets the stage for the mother of all makeovers. 

The Result

Only after Laney conforms to society’s beauty standards does she find the confidence to showcase her creative talents and embrace her authenticity. This transformation also prompts Zack to look beyond appearances, falling for Laney’s warmth and charisma rather than her prom queen potential.

In the end, looks play a minor role in their futures, and as for the high school hierarchy, well, let’s just say everyone gets exactly what they deserve.

Never Been Kissed (1999)

The Makeover

Josie Geller is an undercover reporter who gets a second shot at senior year…as a 25-year-old. This time, with a bar-raising makeover (and some help from her brother Rob), she bats her eyes and uses her brain to get the inside scoop for her story. This generational glow-up opens the door to the popular clique (a sharp contrast to her first high school experience) and puts her in close confidence with a teacher who could be her ticket to a promotion, and maybe even her first kiss.

The Result

While being pretty and popular is fun for a while, Josie soon learns how shallow it all is, and how much true friendship matters. When her makeover-fueled popularity inevitably backfires, she’s forced to reconnect with her real self to win Mr. Colson’s attention and that iconic kiss at the pitcher’s mound (cue “Don’t Worry Baby” by The Beach Boys).

Miss Congeniality (2000)

The Makeover

Miss Congeniality taught us more than why April 25th is the perfect date (not too hot, not too cold, and all you need is a light jacket). It displayed the art of a statement dress (and about a thousand other beauty products) as Agent Gracie Hart undergoes a drastic metamorphosis into pageant contestant Gracie Lou Freebush. Though Gracie isn’t a fan of the disguise, it helps her bond with her fellow contestants all while working undercover for the FBI.

The Result

Despite her aversion to pageant prep, Gracie’s transformation gives her the chance to experience the true power of femininity, find her spark, make genuine connections, and even explore a romance with someone who falls for her true identity rather than her pageant persona. In the end, she gets to keep her badge, and all of Victor’s tips on being a lady!

The Princess Diaries (2001)

The Makeover

SHUT. UP.

Mia Thermopolis is just an average high school sophomore until her grandmother, Clarisse, Queen of Genovia, travels to San Francisco to inform her of her royal blood. With a reimagined makeup routine and the curly-to-straight hair transformation of the century, Mia (now Princess Amelia Mignonette Thermopolis Renaldi) must navigate friendship, crushes, the pressures of teen life, and the possibility of a crown, with Fat Louie always by her side.

The Result

After unwanted attention from the wrong crowd and a rift with her best friend, Lily Moscovitz, Mia realizes the glitz and glam are secondary to the people and places she loves most. This personal evolution, both mentally and physically, guides her towards her royal roots and the person she was always meant to be, with her character shining brightest in the end.

The Devil Wears Prada (2006)

The Makeover

Andrea Sachs just wants to be a serious journalist, but first, she has to pay her dues. That means accepting an assistant position at Runway, a prominent fashion magazine run by the legendary Miranda Priestly. That’s all! 

To survive a year under Priestly’s watchful eye, Andy adapts to the world of tall boots and high fashion under the tutelage of her coworker and confidant, Nigel. 

The Result

Andy’s whirlwind wardrobe upgrade in the Runway closet brings renewed confidence and a career boost, but at the cost of her relationships. This transformation forces her to take a hard look at the life she left behind and the one she’s built as Miranda’s loyal assistant. After facing scorned friends and losing sight of her own dreams, Andy gives away her new clothes (much to Emily’s delight), returns to her old wardrobe, and steps into a writing role as an improved version of the girl who sent in applications prior to her stint as a fashionista. 

More About Film: