Remember in 1999 afterThe Matrixcame out and everyone started dressing like Neo? Walking around the supermarket in a full-length bomber, leather trousers, and black-out sunglasses? Remember how ridiculous they looked? For a while now, filmfashion has been influential, sparking trends and immortalizing looks.
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However, some cinematic characters are a cut above the rest (if you’ll pardon the pun) – they’re so well dressed that it probably strikes awe into the heart of every fashionista. Of course, it helps that their looks are often meticulously crafted by a team of professionals with a limitless budget to work with. Plus, the actors wearing the clothes are usually perfect physical specimens, elevating the looks even higher – the average joe would probably struggle to achieve their aesthetic magnificence. Nevertheless, for those still interested, here are the best-dressed characters in all of cinema.
Updated Jun 08, 2025 by Levana Chester-Londt:For most of these characters, being stylish is part of their personae, and careful planning has gone into each-and-every one of their iconic looks. The fashion realm regularly takes inspiration from popular movies (and vice versa), creating a symbiotic relationship between the two industries. These fashion trends also regularly trickle down into department stores, as high-end runway styles idolized by movie fans transform into affordable everyday wear. One does notneed to cosplay to look liketheir favorite fictional character!
John Wick
Keanu Reeves has influenced fashion-forward viewers for decades, andtheJohn Wickfranchiseis no exception. Dressed in dark tones by the renowned tailor, Luca Mosca (fromParanoia, Skyscraper,andVantage Point), Wick’s impeccable style is rarely compromised by his death-defying work (thanks to his suits' bullet-proof perks!)
The assassin’s melancholic grey and black color palettes are expertly accessorized in each film, with a bright red cuff-link or Carl F Butcherer timepiece added for some extra flair. It’s hard to go wrong with a Milan-born designer carefully calculating every wardrobe choice out on display!
Carrie Bradshaw (Sex And The City)
While this franchise may be more popular as a televisionseries,Sex and the Cityreceived two movie deals. Carrie Bradshaw satisfied expectant fans by modeling some of the most high-end fashion ever featured on the big screen.
From Ralph Lauren, Manolo Blahnik, Timmy Woods, and not forgetting the iconic Vivienne Westwood and Vera Wang wedding dresses, and so much more, Carrie (and friends) unashamedly bring the haute couture runway to Hollywood. Come for the drama, stay for the fashion!
Lucifer (Devil’s Advocate, Constantine, Bedazzled)
No matter the time or place, generally speaking, as soon asLucifer’s name is mentioned, the audience knows they are in for a treat! This fallen angel may essentially be the Big Bad, but he (or she) won’t let a soiled reputation ruin his style.
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Whether dressed up or down (in Elizabeth Hurley’s case) Lucifer will undoubtedly mess with one’s moral compass, by being the most attractive and alluring character on screen. But that’s the name of the game, is it not? Seduce, corrupt, and then move on to the next victim, regardless of howrespectablydressed Lucifer may be.
Christian Grey (Fifty Shades Of Grey)
So while most fanswould rather see Mr. Greywithout any clothes on at all, he is not too shabby when concealed by fabrics either! As a highly reputable businessman, Christian will often don an immaculate grey or navy two-piece suit (with the assistance ofJohnathan Behr tailors in tow).
Christian’s grey sweatpants have become simply iconic, and while it’s not the most high-end fashion, this particular look has caused quite a stir. Even when “playtime” is on the horizon, Christian does not disappoint with his designer Swiss Zimmerli boxer briefs, just to ensure nobody forgets who the boss is here!
James Bond
007 is known for a handful of things: a “vodka martini, shaken not stirred”, wily womanizing, dramatic espionage, and the finest tuxedoes to ever grace the big screen. Throughout the seven iterations of James Bond, from Connery to Craig, his love of a perfectly-cut dinner suit has remained consistent, wowing audiences for decades.
In fact, since each Bond suit is usually supplied by a then-top designer, each film serves as a fantastic reminder of the prevalent fashion of that time. From the shawl-collar dinner jacket of the 1960s to the midnight blue blazer of the 2010s, James Bond has always looked impeccable and provokes the thought “why does this spy always want to stand-out?”
Jim Stark (Rebel Without A Cause)
Fashion represents more than just what clothing items are popular – it reflects society’s prevailing thoughts and feelings. From the tie-dye of the 60s countercultural movement to the gender-bending style of today, fashion is a mirror. And no one captures this better than Jim Stark inRebel Without a Cause.
Portrayed by the iconic James Dean, Stark embodied the generational disenfranchisement endemic to that time (the 1950s). In as much, his signature outfit became something of a uniform for them: the popped collar of a red bomber, the cuffed and aged Levi’s,the scuffed black boots. This wasn’t a ‘style’, it was an act of war, and Stark’s fashion epitomized it superbly.
Wednesday (The Addams Family)
She may not have been the first goth-girl, but she is definitely the most iconic. Whether live-action, animated or even on-stage,Wednesday Addams has helped defined the goth sub-culturefor decades. With her pale skin, long braided pigtails, and (almost) all-black get-up, Wednesday has served as an entry point for millions into counterculture, with her simple take on the style being pre-eminently influential.
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Much like James Bond, Wednesday’s get-up has evolved slightly over time, incorporating nominal changes to reflect contemporary styles. From Lisa Loring’s schoolgirl-esque collar toChloe Grace Moretz’s braids resembling two nooses, Wednesday Addams has always been a style icon.
Jay Gatsby (The Great Gatsby)
Probably the most famous character in all of American literature, Jay Gatsby has been portrayed countless times on-screen, but one aspect has remained resolute: his style has been a testament toluxury, extravagance, and decadence. Each time F. Scott Fitzgerald’s fraudulent hero appears, he’s clad in a new ultra-expensive suit, reflecting the empty wealth of the Roaring Twenties.
From Robert Redford’s perfectly starched all-white get-up toLeonardo DiCaprio’s anachronistic stylings(blame Baz Luhrmann), Jay may be a romantic fraud, but he can be relied on to turn up in some of the best threads this side of Long Island.
Meryl Streep (Any Film She’s In)
It would be easy to point to Miranda Priestly inThe Devil Wears Pradaor Madeline Ashton inDeath Becomes Heror Donna Sheridan inMamma Miaand call it a day, but it would beleaguer a larger point – in every single one of her films,Meryl Streep looks immaculate.
Even as a Witch inInto the Woodsor a detestable grandmother inBig Little Lies, Streep emits a sense of style that can’t be beaten. Is it written into her contract that all her characters need to be dressed to the nines? Or is it that all her characters look amazing because Streep herself looks amazing in anything? Who knows – who cares. When Streep looks this good, it’s not something that can ever be explained.
