Lights, camera, style! Movies have long been a treasure trove of menswear inspiration, featuring iconic looks that transcend the screen and influence wardrobes worldwide. From sharp tailoring to rugged casuals, the silver screen showcases characters whose style defines eras and sets trends.
We’re diving into six cinematic gems that serve as a masterclass in men’s fashion. Whether you’re drawn to the suave sophistication of a tailored suit, the effortless cool of a leather jacket, or the timeless charm of vintage pieces, these films offer a visual feast of sartorial excellence. We’ll explore how each movie’s leading men – from dapper gangsters to rebellious heartthrobs – craft looks as memorable as the stories themselves.
Get ready to take notes on textures, fits, and bold choices that can elevate your wardrobe. Whether you’re revamping your style or seeking a fresh perspective, these films will inspire you to dress with intention and swagger.
Once Upon a Time in Hollywood

Quentin Tarantino’s Once Upon a Time in Hollywood is a love letter to 1960s menswear, with Leonardo DiCaprio’s Rick Dalton and Brad Pitt’s Cliff Booth stealing the spotlight. Rick’s tailored denim jackets and turtlenecks exude retro Hollywood swagger, while Cliff’s laid-back Hawaiian shirts, tight jeans, and cowboy boots scream effortless cool. Their vibrant patterns and bold accessories – like aviators and leather belts – inspire men to embrace nostalgic yet timeless style. The film’s mix of rugged and refined looks offers a masterclass in casual confidence, proving that retro vibes can elevate modern wardrobes with charisma and flair.
The James Bond Series

From Sean Connery’s suave debut to Daniel Craig’s rugged elegance, the James Bond franchise has defined menswear for nearly six decades, capturing a timeless sartorial zeitgeist. Each 007 embodies refinement and debonair masculinity in impeccably tailored suits that exude sophistication or relaxed linen ensembles worn in Caribbean climes. Bond’s wardrobe, sharp tuxedos, crisp shirts, and perfectly knotted ties set a gold standard for polished style. The Bond aesthetic proves that classic elegance, blended with modern flair, remains a powerful blueprint for aspirational menswear.
Fight Club
Fight Club delivers a raw, rebellious take on menswear through Brad Pitt’s Tyler Durden. His iconic style, distressed leather jackets, loud Hawaiian shirts, and worn-in T-shirts, embodies anti-establishment grit. Tyler’s bold, eclectic wardrobe, mixing thrift-store finds with statement sunglasses and combat boots, resonates with men seeking an unpolished edge. The film’s gritty aesthetic, with its blood-stained shirts and rugged denim, teaches that style doesn’t need polish to command attention. Fight Club remains a cult classic for those daring to craft a wardrobe that defies convention.
The Talented Mr. Ripley

Set against the sunlit Amalfi Coast, The Talented Mr. Ripley showcases a masterclass in refined, mid-century menswear. Matt Damon’s Tom Ripley adopts the polished style of the elite, blending Ivy League sophistication with European flair. His wardrobe – crisp linen shirts, tailored blazers, and lightweight trousers in soft pastels – captures the effortless elegance of 1950s jet-setters. Knitted polos and loafers add a relaxed yet luxurious touch, perfect for coastal summers. Ripley’s meticulous style reflects his chameleon-like persona, inspiring men to embrace versatile, timeless pieces. This film’s aesthetic offers a blueprint for blending classic cuts with vibrant settings, elevating everyday sophistication.
The Wolf of Wall Street

Martin Scorsese’s The Wolf of Wall Street is a bold showcase of 1980s and early 1990s excess, with Leonardo DiCaprio’s Jordan Belfort leading the charge. His wardrobe, featuring flashy double-breasted suits, wide-lapel blazers, and vibrant ties, screams unapologetic wealth. Belfort’s power suits in pinstripes and bold colours, paired with crisp dress shirts, are a perfect addition to your business wardrobe. The film’s audacious aesthetic teaches the art of commanding attention through tailored fits and daring patterns. The Wolf of Wall Street offers a masterclass in high-stakes menswear, blending retro opulence with modern charisma for a standout wardrobe.
The Gentleman

Guy Ritchie’s The Gentlemen is a sartorial showcase of bold British menswear. Charlie Hunnam’s Raymond Smith sports sharply tailored three-piece suits in vibrant checks, blending classic Savile Row elegance with modern flair. Colin Farrell’s Coach steals scenes in colourful tracksuits paired with flat caps, redefining casual cool. The film’s mix of tweed blazers, patterned shirts, and sleek overcoats acts as perfect inspiration for men to embrace daring textures and cuts.