The 20 best-dressed film characters ever

Holly Golightly’s black dress from the opening scene of Breakfast at Tiffany’s is arguably the most famous movie costume of all time. Audrey Hepburn would’ve been a style icon regardless of her role in the film, but the ensembles she donned throughout the streets of New York City certainly helped her cause. 

Cher Horowitz lived for fashion. To this day, if you see a blonde woman wearing a plaid yellow set, it’s clear who provided the inspiration. With duds from Alaïa, Calvin Klein, and more, Cher, as a high-schooler, was more stylish than most adults (though it does help that her father was an incredibly wealthy attorney). 

It’s all but been confirmed that Miranda Priestly was inspired by Anna Wintour, and after seeing the movie, Wintour had to have been complimented (by the style, that is — not necessarily the icy behavior). Whether she was accosting her employee for her inability to fly her home during a hurricane or lecturing the same employee on the history of cerulean, Miranda was well-dressed.

Andy Sachs learned a lot from her time at Runway — particularly how to dress. Andy went from a fashion novice to a style veteran in a matter of months, and every single one of her outfits would look good today, including the Chanel boots. 

Vivien Leigh stunned in her role as Scarlett O’Hara in Gone with the Wind. Her dresses screamed Southern belle, and she clearly knew how to accessorize. Whether she accentuated her waist with a red belt or topped off her ensemble with a hat, Scarlett was making a fashion statement. 

Elle Woods proved that just because most people in your profession dress according to a certain palette doesn’t mean you have to. Her pink dress for her appearance at court will forever be iconic. 

The white and blue outfit, the red dress, the blonde wig — Vivian Ward’s outfits and accessories that make her so well-dressed go on and on. Vivian had personal style before she had access to the best clothing money could buy, and she always stayed true to herself no matter what she could afford. 

Sure, it’s easy to go down as one of the best-dressed movie characters of all time when you’re played by Audrey Hepburn, but Sabrina had style regardless. Her stunning black and white dresses, darling caps, white gloves, and subtle yet beautiful jewelry choices helped us understand Sabrina as a character and made us wish we could raid her closet. 

There are plenty of well-dressed men in film history, too, like Jay Gatsby. His three-piece suits were well-tailored and worn in colors that complemented his coloring. While his accessory of choice seemed to be a coupe cocktail glass, he was just as appealing wearing bow ties and pocket squares. 

Lorelei Lee could’ve worn the pink dress and gloves for the entirety of Gentlemen Prefer Blondes, and she’d still be known as one of the best-dressed film characters of all time. But in case you need more evidence, see the orange dress and purple ensemble she also donned in the film. 

Another well-dressed man from film history is James Bond. No one has made espionage look as glamorous as he has, and that’s saying something since nearly every film depicting the action has tried to romanticize it. We have to imagine shooting guns and chasing cars in a tuxedo would be difficult, but Bond makes it look easy. 

The two most famous red jackets belong to Michael Jackson and Jim Stark in Rebel Without a Cause. James Dean’s famous look proved that sometimes it’s best to keep it simple regarding fashion. 

Cruella De Vil’s fashion sense was great to begin with, but it only improved with each iteration of the iconic villain. By the time Cruella rolled around, the character’s style was fully defined, with distinct fabrics, favored patterns, and close attention to detail marking what makes her so well-dressed. 

Deena Jones embodied the ultimate diva style, and her fashion range was as sprawling as her vocal range. She also proved that you can wear the exact same outfit as somebody else and still have a personal style. No matter who she was next to, she stood out in the crowd. 

It’s only fitting that one of the best-dressed TV characters has a place on the list of the best-dressed film characters since she’s also part of one of the few TV series to garner a movie spin-off (and an entire film series, at that). Carrie Bradshaw was just as well-dressed in the Sex and the City films as in the series. 

The real Cleopatra was most certainly well-dressed, and if she wore anything like what Elizabeth Taylor wore in the movie, she was probably a major fashion inspiration for her royal subjects. She also knew how to accessorize and had stunning glam. 

It’s easier for men to be considered well-dressed than women. There are far fewer options for what to wear, but that hasn’t stopped the Adam Sandlers of the world, and therefore, we must applaud characters like Thomas Crown. He definitely knew how to dress. 

Crazy, Stupid, Love’s Jacob Palmer has such good style he’s able to transform his friend Cal into a style maven of his own. And whether he’s wearing something casual or formal, he looks like he was plucked straight off a runway. 

The two best black bobs in film history belong to Edna Mode and Mia Wallace. Mia ascended to fashion icon status over Edna since she paired her bob with button-downs and t-shirts, but we have to imagine that thanks to her black and white palette and lack of capes, Edna approved. 

They said it in the film themselves: Astrid Leong-Teo is a fashion icon. The Crazy Rich Asians character was exuding quiet luxury before it became mainstream, and she only looked better by the end of the film when she gained the confidence to be unapologetically her stylish self.