Remember in 1999 after The Matrix came 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, film fashion 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 September 18, 2022 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 not need to cosplay to look like their favorite fictional character!

John Wick

strangest weapons John Wick used

Keanu Reeves has influenced fashion-forward viewers for decades, and the John Wick franchise is no exception. Dressed in dark tones by the renowned tailor, Luca Mosca (from Paranoia, Skyscraper, and Vantage 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)

Cinematic Fashion Icons Carrie Bradshaw Sex and the City Sarah Jessica Parker

While this franchise may be more popular as a television series, Sex and the City received 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)

Cinematic Fashion Icons Lucifer Bedazzled, Constantine, Devil's Advocate

No matter the time or place, generally speaking, as soon as Lucifer'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 how respectably dressed Lucifer may be.

Christian Grey (Fifty Shades Of Grey)

Cinematic Fashion Icons Christian Grey Fifty Shades of Grey Jamie Dornan

So while most fans would rather see Mr. Grey without 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 of Johnathan 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

James Bond 007 No Time to Die

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 in Rebel 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)

Wednesday Addams History of The Addams Family Tim Burton, Netflix

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-culture for 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 to Chloe 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 to luxury, 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 to Leonardo 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 in The Devil Wears Prada or Madeline Ashton in Death Becomes Her or Donna Sheridan in Mamma Mia and 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 in Into the Woods or a detestable grandmother in Big 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.

Source: Studypool

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