Fashion can truly make an impression with any character you’re trying to get across; especially with the figures we’re about to discuss. Clothing is definitely not optional, it’s a way of life for some of the snazziest dressers in all of cinematic history. So straighten your tie, smooth out your sweater, and slip on your glasses to take a look at these shining examples of sartorial supremacy.
James Bond (The James Bond Movies)
How can you not admire the costume design throughout every era of James Bond movies? No matter your chosen actor for the job, 007 has made his way into the world with a fine style that matches his cutting wit. His fashion is forever.
Holly Golightly (Breakfast At Tiffany’s)
Holly Golightly (Audrey Hepburn) became a fashion icon for the ages in 1961’s Breakfast at Tiffany’s. It’s certainly not hard to see why, as Hubert De Givenchy and Edith Head’s talents gave this movie its signature looks; chiefly among them some little black dresses that launched a thousand party outfits.
Sam “Ace” Rothstein (Casino)
How mythic is the wardrobe of Robert De Niro’s Sam “Ace” Rothstein from Casino? There are whole YouTube videos and posters designed to show them off. Not to mention even some of the oversized glasses that Martin Scorsese’s protagonist wears during the film have become the stuff of legend. Better still: Ace isn’t afraid to wear pink, and it suits him to a tee.
Lorelei Lee (Gentlemen Prefer Blondes)
Sure, as a musical showgirl, it was technically the job of Lorelei Lee (Marilyn Monroe) to always be on point with her looks. But at the same time, Gentlemen Prefer Blondes certainly snazzed her up in everyday life, thanks to some beautiful use of patterns and color. And of course, who could forget the iconic pink dress Monroe wore during “Diamonds Are A Girl’s Best Friend?”
Django (Django Unchained)
Once he entered the world of bounty hunting, Django (Jamie Foxx) took a lot of the advice Dr. King Schultz (Christoph Waltz) gave him to heart. And part of that package was the note that your wardrobe is basically your costume for the moments in your life. Everything from rough and tumble western wear to a natty blue velvet suit with ruffles resulted from that viewpoint, and we’re all the greater for it.
Miranda Priestly (The Devil Wears Prada)
If one is going to help make the decisions that puts cerulean sweaters on the backs of those who pretend to hate fashion, one needs to look like they’ve earned that right. The Devil Wears Prada’s Miranda Priestly (Meryl Streep) definitely earned that right, and then some. While Streep gave up Method acting because of the character’s miserable nature, her style never looked anything less than top-flight.
Caesar Flickerman (The Hunger Games Trilogy)
Oh Stanley Tucci: the respected actor that, early in his career, was a beefcake model for Levi’s. The man’s style sense has never left him, with Caesar Flickerman from The Hunger Games trilogy being one of his more outlandish cases of style. Bursting with color that matched his energy, it’s hard to hate Panem’s prince of propaganda.
Cruella DeVil (Cruella)
Cruella reinvented the Disney villain from 101 Dalmatians into someone who dug a lot more than Dalmatian spots. Emma Stone’s titular icon of villainy actually changed her tone in this reimagining, setting her sights on revenge in the fashion world, and adopting a sort of punk rock couture aesthetic to do so. Vengeance looked amazing in her hands.
Jinx (Die Another Day)
Yes, Halle Berry’s freezing James Bond entrance in Die Another Day showed her rocking an impressive bikini. But her outfits throughout the rest of the film didn’t slouch either, especially the red leather number that kept her warm in the ice palace of Gustav Graves (Toby Stephens). Though it probably also came in handy that time she was nearly carved up by lasers too.
Charon (The John Wick Movies)
The entire John Wick universe is dressed to the nines, exuding a style profile that puts most action movies to shame. But if I were to highlight anyone, I’m afraid it’d have to be Charon, played by the late great Lance Reddick. Then again, The Continental is one of those places where you always have to be on your fashion game; so maybe this choice was easier than I thought.
Emily Nelson (A Simple Favor)
Paul Feig’s cinematic adaptation of A Simple Favor saw Blake Lively dipping her toe into all corners of the fashion spectrum. Through looks borrowing from both traditionally masculine and feminine modes, it all looked deadly beautiful throughout her neo-noir character’s arc.
The Protagonist (Tenet)
Inspired by Sean Connery’s James Bond fashion, Tenet costume designer Jeffrey Kurland crafted fashions for The Protagonist (John David Washington), as well as his accomplice Neil (Robert Pattinson) that evoked the classic era of 007. Kind of fitting for a movie where incremental time travel is the game, and Christopher Nolan’s discipline for panache is also very much present.
Astrid Leong (Crazy Rich Asians)
Astrid Leong (Gemma Chan) has a heart of gold, and the fashion sense to match it. Throughout the entirety of Crazy Rich Asians, she never failed to show up in some of the most gorgeous outfits; even in moments where her heart was breaking in devastating detail. Every time she’s on screen, it’s like watching a fairy tale.
Jay Gatsby (The Great Gatsby)
When you’ve got a character that’s described as “the man in the cool beautiful shirts,” your costume design needs to measure up. Director Baz Luhrman’s adaptation of The Great Gatsby used the talents of costume designer Catherine Martin to do just that, giving Leonardo DiCaprio’s interpretation of F. Scott Fitzgerald’s tragic character the finest threads money could buy.
Tracy Chambers (Mahogany)
Mahogany’s Tracy Chambers (Diana Ross) has aspirations to be a fashion designer herself. So it’s only fitting that she not only found her way into modeling, but also onto this list of snazzy dressers. Epitomizing the color and opulence of the disco era, her cautionary tale saw Tracy looking absolutely fabulous, even in her most dire moments.
Nigel (The Devil Wears Prada)
If you haven’t heard it before: Stanley Tucci is a man of great fashion. One of the best examples of this is the role of Nigel in The Devil Wears Prada. While he’s a bit nicer spreading the gospel of fashion than his boss Miranda (Meryl Streep), Nigel doesn’t let up in his keen eye for style in the process.
Jackie Brown (Jackie Brown)
Whether she’s coming home from flying the friendly skies, or keeping one step ahead of her criminal compatriots, Jackie Brown (Pam Grier) always looks fantastic. Of course, her striking blue uniform for her day job is what’s always stuck out in Quentin Tarantino’s film. That being said, Ms. Grier’s civilian clothes are no slouch either, especially in that food court outfit where she’s stylishly wearing a Kangol cap.
Thomas Crown (The Thomas Crown Affair)
Billionaire by day and thief in his downtime, The Thomas Crown Affair’s titular rogue is always sharply suited for the occasion. Pierce Brosnan’s James Bond movies certainly set a similar expectation, but this 1999 remake gave the actor some room to roam; even if he wasn’t contractually allowed to be seen in traditional black tie.
Foxy Cleopatra (Austin Powers in Goldmember)
Borrowing from the rich fashion history of blaxploitation heroines, Austin Powers in Goldmember gave Foxy Cleopatra a whole lot of looks for a whole lot of woman. Then again, when you’ve cast Beyoncé as your female lead, it’s kind of hard to make her look anything other than stunning. Still, an abundance of color and flare is seen through every costume change in this spy movie spoof.
Patrick Bateman (American Psycho)
‘80s business attire was a unique beast that had stock brokers ready to step out into the night once the closing bell had rung. Using GQ and Esquire as a bible, it’s no wonder how American Psycho’s Patrick Bateman (Christian Bale) always looked as sharpened as a kitchen knife. Though spare a thought for the man’s dry cleaners, as he does have a bit of a temper.
Niobe (The Matrix Reloaded & Revolutions)
Pretty much everyone in The Matrix is a snazzy dresser, especially when they're in The Wachowski's cyberspace playground which gives the film its title. But extra credit has to be given to Niobe (Jada Pinkett Smith), as she's not a simple black-and-white dresser. With a long red coat that sets her apart from the rest, reflecting her colorful wardrobe in the real world, The Matrix Reloaded and Revolutions were a bit brighter when she battled it out on screen.
Marvello Rubini (La Dolce Vita)
There are certain fashion touchstones of cinema history that will never, ever go out of style. And one such look is the classic suit and sunglasses worn by Marcello Mastroianni’s Marvello Rubini, in one of the greatest Italian movies of all time, La Dolce Vita. You can never go wrong with that black suit, but the eyewear that Federico Fellini's protagonist wears throughout the picture really clinches the win every time.
Elle Woods (Legally Blonde)
Pink is a hard color to work with because, in the wrong context, it could be seen as much too loud. Meanwhile, Legally Blonde icon Elle Woods (Reese Witherspoon) never met a shade of this pigment she didn’t like. Her signature hue throughout both films, this legal eagle soars high in the sky with flying colors; and it never goes out of style.
Danny Ocean (Ocean’s Eleven)
A friend once told me, “no one looks as cool as Danny Ocean getting out of prison.” Judging by the look George Clooney’s Ocean’s Trilogy mastermind is rocking at the beginning of that first movie, it’s hard to argue. It’s even more difficult to argue that through all three films, the man isn’t bringing his A-game every single time he steps out.
Annie Hall (Annie Hall)
Blazing a trail for women’s fashion, Annie Hall’s eponymous figure took what was traditionally seen as “men’s clothing” and used it as her own statement to the world. Played brilliantly by Diane Keaton, her keen fashion sense was matched by her wicked wit, more often than not being deployed against lovelorn Alvy Singer (Woody Allen).
Frank Abignale (Catch Me If You Can)
What is it about confidence crooks that gives them such brilliant fashion sense? Perhaps when Frank Sr. (Christopher Walken) told his young son Frank Jr. (Leonardo DiCaprio) about how those Yankees pinstripes bedazzle the competition, he was onto something. As a result, Catch Me If You Can’s “real fake” is seen kitted out in everything from pilot’s uniforms to orange sweaters, and he’s always looking dapper as a result.
Reynolds Woodcock (Phantom Thread)
“Meticulous” is one word that sums up Phantom Thread’s Reynolds Woodcock (Daniel Day-Lewis). Paul Thomas Anderson’s dark comedy about romance, fashion, and all the illnesses in between saw the Academy Award-winning legend retire in literal style, playing a fashion designer who would never step foot out the door with even a hair out of place.
Ginger McKenna (Casino)
Martin Scorsese’s Casino shows Las Vegas through some of its most tumultuous years. And one of the indicators of how time passes is in the fashion, as Ginger McKenna (Sharon Stone) goes from good-time gal to the trusted wife of casino manager Sam “Ace” Rothstein (Robert DeNiro). Gliding through the years with an effortless eye, Ms. Stone’s costumes maintain an air of control, even when her character seems to be losing that very grasp in life.
Cher Horowitz (Clueless)
Cher Horowitz (Alicia Silverstone) is the ‘90s, period. A fashionista who made something like yellow with black plaid into a work of art, our Clueless hero is anything but when she’s putting together her outfits. Who could ever forget the first time they saw some of Cher’s most signature looks in play?
Jules Winfield (Pulp Fiction)
The look of a simple black suit cannot be understated, especially when someone like Samuel L. Jackson is the person wearing it. As imposing fixer Jules Winfield in Quentin Tarantino’s Pulp Fiction, Jackson wears this outfit for most of the movie’s running time; save for those sequences taking place after one catastrophic accident. Even in a random t-shirt and shorts, the man knows how to make an impression and keep all the Fonzies in the room cool.
Rachel Chu (Crazy Rich Asians)
While Rachel Chu (Constance Wu) isn’t from the same sort of world as the family of her boyfriend Nick (Henry Golding), that doesn’t stop our Crazy Rich Asians lead from engaging in a makeover. As the film progresses, and through some friendly makeover advice from her best friend (Awkwafina), confidence and fashion are both boosted in equally impressive ways.
Trent (Swingers)
Most would remember the lead characters of Swingers for their big band revival threads that play a big part in their trip to Vegas. However, if you look at the styles that Trent Walker (Vince Vaughn) displays throughout the movie, he is a true example of making anything work. Even his outbursts in a late-night dining situation look sharp, as he knows how to crush a look when he’s relaxed or when he’s switched on.
If you were looking for some style icons to look up to for a near-future wardrobe refresh, look no further than these movie mavens. With all sorts of looks at work for all types, there’s bound to be something here that could give you the upgrade you’ve been hoping to achieve. And now that you’ve read through this handy guide to such delights, don’t you think you’ve earned it?
