Johann Hunt
Style on screen is never random. Every outfit tells part of the story, and in some cases, becomes the story. Some looks just hit differently and end up influencing culture far beyond the theater. Over time, they become fashion moments in their own right. Here’s a round-up of 20 characters who wore it best.
Holly Golightly In “Breakfast At Tiffany’s”
One dress is all it took to seal Holly Golightly’s place in fashion history. The sleek black Givenchy gown, styled with oversized sunglasses and pearls, became shorthand for effortless elegance. It’s been reimagined in editorials and even auctioned for over $900,000.
James Bond In “Casino Royale”
Daniel Craig’s Bond in “Casino Royale” gave the classic look a sharper edge. Around 30 custom suits were created, all helping redefine modern menswear. Tom Ford saw a sales boost, and watchmakers took notes. Bond’s wardrobe was a recalibration of what suave meant in the 2000s.
Cher Horowitz In “Clueless”
There’s memorable, and then there’s Cher’s yellow plaid suit. It instantly became a cinematic style staple. Her digital wardrobe system was fun, but also a surprisingly forward-thinking nod to future tech. Between that and the 60-plus outfit changes, “Clueless” turned its six-figure costume budget into a legacy.
Miranda Priestly In “The Devil Wears Prada”
Miranda Priestly didn’t need dialogue to command attention because her wardrobe did that first. Built with pieces from major fashion houses, her look was editorial. Meryl Streep had a hand in fine-tuning it. What emerged was a character that made the fashion world feel both intimidating and strangely familiar.
Jay Gatsby In “The Great Gatsby”
There was always more to Gatsby’s suits than their shimmer. Pale hues paired with precise cuts came to life thanks to Brooks Brothers, who designed hundreds of bespoke looks. The impact was immediate: Gatsby parties, 1920s themes, and a full-on revival of vintage men’s style.
Elle Woods In “Legally Blonde”
For Elle Woods, pink was a declaration. Every blush and fuchsia piece she wore added another layer to her story. With over 40 outfits in the film, her style was both playful and purposeful. Later, Broadway designers borrowed those visuals and pink surged back into the mainstream.
Indiana Jones In “Raiders Of The Lost Ark”
Indiana Jones dressed to survive. Still, the fedora, worn leather jacket, and satchel became unforgettable. Military influences laid the foundation, yet Harrison Ford’s personal touches turned it into something cinematic. That look became the blueprint for every adventurer who followed on screen and off.
Tyler Durden In “Fight Club”
Nothing about Tyler Durden’s style played it safe. The red leather jacket became his armor, paired with tees and prints that clashed and commanded attention. Streetwear brands eventually picked up the thread. That same jacket now still circulates as a cult fashion piece, unapologetic and bold.
Dickie Greenleaf In “The Talented Mr. Ripley”
Some characters wear wealth casually, and Dickie did it better than most. His Riviera wardrobe breathed privilege and ease. Jude Law’s performance turned those looks into a vibe that spread into European menswear collections. Vintage shades and boat shoes saw a spike.
Satine In “Moulin Rouge!”
Spectacle was Satine’s world, and her wardrobe made sure no one forgot it. Catherine Martin designed more than 400 intricate looks, each one bursting with drama and detail. Her unforgettable red gown shimmered with over a thousand Swarovski crystals. These reflected her fragility and fire, all stitched into glittering fabric.
Vivian Ward In “Pretty Woman”
Vivian Ward’s story pivoted the moment she stepped into that red opera gown. The dress was a turning point. Marilyn Vance, the film’s costume designer, intentionally used actual designer pieces to deepen the realism. The polka-dot number she wore earlier was also iconic, with its own life in fashion circles.
Annie Hall In “Annie Hall”
There was a quiet rebellion in Annie Hall’s clothes. Menswear-inspired but never borrowed, her baggy trousers and layered vests redefined casual cool. Diane Keaton wore her own pieces, and it changed everything. Tailored suits for women went mainstream, and fashion started asking new questions about self-expression and identity.
Tony Manero In “Saturday Night Fever”
All it took was one white three-piece suit and a dance floor. Tony’s look captured a cultural moment that pulsed with music and Saturday night highs. That suit turned into a global fashion icon, which revived formal menswear for partygoers. Its popularity crossed oceans, eventually selling at auction for $260,000.
Cruella De Vil In “101 Dalmatians”
Cruella de Vil’s look was as fierce as her personality. Glenn Close leaned into excess, wearing towering fur coats that pushed costume design into fashion territory. One coat alone weighed around 45 pounds. Over time, her black-and-white visual world influenced punk and goth styles.
Rachel Chu In “Crazy Rich Asians”
Elegance followed Rachel Chu through every scene, quiet but undeniable. Her wardrobe choices felt deliberate and never overdone. The film’s costume work featured more than 30 designers, many gaining visibility like never before. The fashion on screen brought Asian couture into broader conversations around craft and design.
Regina George In “Mean Girls”
Fashion in “Mean Girls” had a queen, and it was Regina. Her wardrobe captured the early 2000s so well that it became its own fashion archive. The use of actual teen brands grounded the style in reality. Years later, people were still studying her outfits.
Cleopatra In “Cleopatra”
Elizabeth Taylor’s lavish gowns set new records for costume design. Sixty-five costume changes and a $190,000 wardrobe budget made headlines. Designers like Versace took notes. Her look redefined what historical fashion could be in film and launched a wave of Cleopatra-inspired looks in high fashion.
Patrick Bateman In “American Psycho”
Nothing about Patrick Bateman’s wardrobe was accidental. His Armani suits mirrored a life ruled by precision and image. That obsession with appearance even shaped real-world fashion. Wall Street embraced the sleek tailoring. Men’s skincare routines and luxury accessories followed, all part of chasing that calculated perfection.
Sugar Kane In “Some Like It Hot”
On stage, Sugar Kane shimmered. Behind the sparkle, though, was a masterpiece of costume artistry. Orry-Kelly’s sequin-covered gowns for Marilyn Monroe supported the film’s light, comedic tone. His Oscar win confirmed their impact. The effect was lasting: flapper fashion returned, and Sugar’s style became a quiet staple of cinematic glamour.
Rick Blaine In “Casablanca”
Rick’s trench coat became film noir fashion shorthand. Paired with a fedora, the look set the standard for grit and mystique on screen. The original coat later sold for around $10,000, but its value went far beyond auction numbers. Worn during World War II, it influenced real soldiers and civilians alike.