THE MOST FASHIONABLE FILMS OF ALL TIME

Fashion has always belonged to the movies. Long before Instagram moodboards and TikTok trend cycles, film was where style was mythologised, outfits immortalised not because they were practical, but because they meant something. A character’s clothes told you who they were, what they wanted, and where they were headed, often before they spoke a single line. 

These are not just films with good costumes. These are fashionable films, the ones that shaped silhouettes, launched It-Girls, rewired wardrobes, and still influence how we dress today.

The Talented Mr. Ripley

If quiet luxury had a cinematic origin story, this would be it. Set against the sun-drenched backdrop of 1950s Italy, The Talented Mr. Ripley delivers a masterclass in effortless privilege dressing: linen shirts worn just a little too open, soft tailoring, silk scarves tied without trying. Jude Law’s Dickie Greenleaf remains one of the most influential style archetypes in film history - a blueprint for inherited taste and nonchalant wealth. This is fashion that whispers, not shouts. The kind that looks better the less you think about it.

Marie Antoinette

Sofia Coppola didn’t just make a period drama - she made a moodboard. With candy-coloured gowns, towering wigs, and a now-iconic anachronistic soundtrack, Marie Antoinette reframed historical fashion through a modern lens. It’s indulgent, excessive, and deliberately unserious - a reminder that fashion can be playful, political, and a little bit bratty all at once. Still referenced on runways, Pinterest boards, and Gen-Z styling TikToks, this film proved that fantasy dressing never really goes out of style.

CNo list like this is complete without Clueless - the film that taught an entire generation how to dress, shop, and pronounce Alaïa correctly. Cher Horowitz’s wardrobe is iconic not just because it’s bold, but because it’s intentional. Every look is styled with precision: matching sets, knee-high socks, structured tailoring softened by colour and charm. It’s fashion as confidence, fashion as identity, fashion as fun. Thirty years on, the influence is still everywhere - from Miu Miu runways to micro-minis worn with authority.

American Gigolo

This is where menswear changed forever. American Gigolo introduced Giorgio Armani’s relaxed tailoring to the mainstream, redefining masculinity on screen. Richard Gere’s wardrobe - fluid suits, open shirts, neutral tones - felt sensual, modern, and quietly radical for its time. It’s impossible to talk about contemporary men’s fashion without tracing the line back to this film. Proof that sometimes, all it takes is a perfectly cut jacket to shift culture.

Eyes Wide Shut

Dark, decadent, and deeply unsettling - Eyes Wide Shut uses fashion as psychological tension. Nicole Kidman’s wardrobe is sleek, icy, and impossibly chic; Tom Cruise’s tailoring is rigid, almost suffocating. Costumes here aren’t about aspiration - they’re about control, power, and what’s left unsaid. The result is a film that feels perpetually referenced in high-fashion editorials, long after its release.

A Single Man

When a fashion designer directs a film, it shows. Tom Ford’s A Single Man is meticulous to the point of obsession - every frame styled, every outfit deliberate. The suits are sharp, the colour palette controlled, the aesthetic emotionally loaded. It’s fashion as grief, fashion as memory, fashion as restraint. A cult favourite for good reason.

Bonnie and Clyde

Few films have created a fashion archetype as enduring as this one. Faye Dunaway’s Bonnie brought berets, bias-cut skirts, and ’30s tailoring back into the cultural imagination - a look that still resurfaces whenever fashion leans romantic, rebellious, or slightly dangerous. It’s the original It-Girl uniform.

Phantom Thread

Phantom Thread is fashion at its most obsessive. Paul Thomas Anderson’s portrait of a fictional 1950s couturier is less about clothes as spectacle and more about clothes as control, ritual, and intimacy. The gowns are exquisite, yes - but it’s the process that lingers: the fittings, the pinning, the silent authority of the atelier. This is fashion stripped of glamour and reassembled as devotion. It speaks to anyone who understands that clothing isn’t just about appearance, but about power dynamics, authorship, and the cost of perfection. Quiet, chilling, and devastatingly chic.

The Devil Wears Prada

No film has shaped modern fashion literacy more than this one. Period. The Devil Wears Prada didn’t just show fashion - it translated it. Suddenly, the industry’s inner workings, hierarchies, and unspoken rules were part of the cultural mainstream. The cerulean monologue alone should be taught in schools. Miranda Priestly remains fashion’s most terrifying and magnetic figure, while Andy Sachs’ transformation is less about clothes and more about self-awareness. It’s a reminder that fashion is never superficial - it’s a language, and fluency comes at a cost. Still quoted. Still referenced. Still correct.

House of Gucci

Messy? Yes. Fashionable? Absolutely. House of Gucci leans fully into excess - fur coats, shoulder pads, logos worn loudly and without apology. It’s not a subtle film, but then neither was the era it depicts. This is fashion as ambition, status, and spectacle. Lady Gaga’s Patrizia Reggiani dresses for power, not taste - and that’s precisely the point. The film understands that fashion doesn’t always need refinement to be influential. Sometimes, it just needs confidence. Camp, chaotic, and endlessly memorable - exactly as fashion history often is.

The Royal Tenenbaums

Few films have produced a fashion character as instantly recognisable as Margot Tenenbaum. Gwyneth Paltrow’s wardrobe is deceptively simple: fur coat, striped dress, loafers, heavy eyeliner, hair clipped back and untouched. It’s repetitive by design - a uniform that mirrors Margot’s emotional stasis and quiet detachment. Fashion here isn’t about transformation, it’s about refusal. Margot is also widely noted for carrying a Hermès Birkin throughout the film - worn casually, unremarked upon, and decidedly pre-It-bag hysteria. Released in 2001, The Royal Tenenbaums captured the Birkin in its insider era: expensive, yes, but not yet a cultural trophy. It reads as inherited taste rather than overt status signalling. The result is a look that has become endlessly referenced, copied, and mythologised. Proof that true style impact doesn’t come from constant outfit changes - sometimes it comes from committing to one perfectly judged look and never explaining it.

Why Fashion Films Still Matter

Fashionable films don’t just reflect style - they shape it. They teach us how to desire, how to dress for fantasy, how to project identity through clothing. In an era of fast trends and algorithmic taste, these films remind us that style is most powerful when it’s tied to storytelling. They’re not just things to watch. They’re references. They’re education. They’re archives. And if you’re looking to channel any of these cinematic wardrobes today? You know where to start. Shop Rewind Vintage Affairs’ curated edit - because the best fashion moments never really end.