Directed by Anthony Minghella, The Talented Mr. Ripley follows Tom Ripley (Matt Damon), a con man and forger who through a series of events is enlisted to track down Dickie Greenleaf (Jude Law) by his magnate father. Through the course of the movie Ripley quickly becomes obsessed with Greenleaf, jealous of his wealth, social stature and, yes, his wardrobe. While Ripley’s near-constant lying and machinations propel the plot, clothing and style permeate the film, a constant reminder of Greenleaf’s privilege—and Ripley’s lack thereof.

Taking place predominantly in Italy and the bordering Adriatic coast, the film’s clever mix of 1950s American sportstwear with Italian sartorial panache lead to some incredible wardrobe moments. Linen trousers with a knit polo, Bermuda shorts with high-end Gucci loafers, silk shirts and suede jackets, all allude to classic menswear done right. Given the film takes place in Venice, leisurely boat rides and scooter scenes were a must. But perfectly scuffed white deck shoes on Greenleaf’s schooner and Paltrow’s perfectly billowing trench coat on the back of the Vespa bring these scenes to life. More than simply fill a scene, in the film wardrobe adds much needed subtext. Ripley’s suit, for instance, is a clear example of Ivy style—a nod to his fabricated alma mater.

While on paper this all may sound a bit passé, on film this lavish, languid expression of mid-century American expats is incredibly enticing—particularly in our current quarantined paradigm. Featuring numerous standout actors in their prime (Phillip Seymour Hoffman and Gwyneth Paltrow both play prominent roles) The Talented Mr. Ripley offers escapism, style inspiration and Oscar-worthy performances all packaged within a highly-digestible thriller.

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One of Martin Scorsese’s most controversial films, 30 years later it’s hard not to love Goodfellas. While critically praised, the film was publicly lambasted, decried for its supposed celebration and adoration towards mob life and gangsters in general. Though still a relative commercial success, the film pales in comparison to Scorsese’s more recent ventures.

Released in 1990, the film centers around the life of Henry Hill (Ray Liotta), an aspiring gangster who, despite a lack of Italian heritage—he’s only Sicilian on his mother’s side, not good enough to be “made”—aims to be a top mob boss. While the story revolves around his crew and the local crime family, as far as style is concerned, Hill is top dog. From the moment Hill shows up in a double-breasted cream suit, it’s clear he avoids the typical mobster fashion cliches. While peers like James “Jimmy The Gent” Conway (Robert DeNiro) and Tommy DeVito (Joe Pesci) have their moments, it’s clearly Hill who has not only fashion sense, but innate class. Unlike Jimmy or Tommy, Hill’s primary motivation towards crime is the glamorous lifestyle it affords him. Hanging in the Copacabana in tailor-made suits over tightly knit polos and oversized sunglasses is a dream come true, a life—and wardrobe—only drug profits, racketeering and fraud could afford him.

While the film spans years—the real life Henry Hill was a mob figure from 1955-1980 before turning FBI informant—the outfits truly hit a stride in the late-'60s to early-'70s, when following some major scores Hill and company make a name for themselves. In a tan suit with red tie, an olive green suit at the bar and a sharkskin suit over a black pinstriped Italian knitted polo, Hill is half-gangster, half-American business magnate, with his shoddy crimes well hidden underneath a polished exterior. Even casual looks like oxblood leather jacket or adidas tracksuit in prison have an air of glamour, most likely simply because Liotta is so compelling. As for the film itself, it’s an undeniable classic, just as quotable and watchable today as it was three decades ago. Some of Liotta, Pesci and DeNiro’s looks may not hold up—the three button suit is a tough call for anybody—but the film itself is unimpeachable.

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Nicholas Winding Refn is divisive. His movies drive both viewers and critics insane, garnering standing ovations at film festivals one moment while prompting hundreds to literally vacate their local theaters the next. His one universally beloved film, though, always delivers.

Released in 2011, Drive, follows the unnamed Driver, a mechanic/stunt double/stunt car/getaway car driver for hire who is ensnared in a complex criminal web involving his love interest, her husband, the local mafia and himself. Of the many film’s many stand-out qualities—neon-tinted cinematography, immaculate soundtrack, strong supporting cast—two qualities stand out: Gosling’s performance and, of course, his wardrobe.

While The Notebook propelled Gosling to heartthrob status, it was Drive that kicked off an indie film sprint that served as proof he had the acting chops to match his chiseled physique. With almost no dialogue, The Driver manages to communicate with love interest Irene (Carey Mulligan) and her parolee husband Standard Gabriel (Oscar Isaac) with ease, a testament to Gosling’s performance and Winding Refn’s smart editing. The eerie soundtrack and long, almost silent scenes create a foggy, moody narrative, further complicating the film's already convoluted plot structure. Despite a loose narrative and often misleading transitions, even 10 years later, the film still rewards those willing to wait for its climax. With a straightforward protagonist and clear stakes, the film delivers every time.

In line with his simple, straightforward nature, Driver only has one outfit. Inspired by the 1950s Korean souvenir jackets Gosling himself regularly wore at the time, costume designer Erin Benach commissioned 27 identical jackets for the film. A reversible white sukajan with a massive embroidered scorpion on the back, the jacket became not only the most popular Halloween costume of that year, but helped kick off a sukajan trend in fashion spaces, when every brand under the sun produced its own version. While the trend has since died, Gosling’s blood, dirt and motor oil stained bomber, black jeans and derbies is still one of the most memorable on-screen fits in recent film history.

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A year after Drive, Gosling’s indie-streak continued with The Place Beyond The Pines. Directed by Derek Cianfrance, the film—with an all-star cast including Eva Mendes, Bradly Cooper, Ray Liotta and Ben Mendelsohn, among others—was clearly made with awards season in mind.

That said, a tepid reception at film festivals and lack of critical praise meant the movie was a bit of a dud, no doubt at last partially due to its misleading marketing campaign. While initially billed as a parallel between motorcycle stunt rider Luke Glanton (Ryan Gosling) and former attorney turned local cop Avery Cross (Bradley Cooper), despite extensive promotion throughout the trailers, Gosling’s character exits the film at roughly the 40 minute mark. The unceremonious removal of the lead is no doubt jarring, but the film itself is worth a watch for Glanton alone.

The first section of the film follows Glanton who, after returning to a small town with his traveling circus, reconnects with a former lover and their now infant son. A wistful, aimless motorcycle rider suddenly thrust into parenthood, Glanton needs cash fast to support his newfound family, and so turns to a life of crime. The character’s style is not so much a reflection of who he is in the present, but rather his years as a hard-riding nomad. Perfectly distressed heavy metal T-shirts, destroyed jeans and perfectly fitted leather moto pants all allude to Glanton’s sordid past. Once again working with Erin Benach—the same costume designer as Drive—the two sourced rare, high-end vintage pieces from some of the most notorious dealers in Los Angeles to ensure Glanton felt truly authentic.

Make no mistake, The Place Beyond The Pines is by no means a perfect movie. It has its bevy of issues and shortcomings. But, that aside, Glanton is a menswear icon, peak Tumblr-bate and a perennial reference for designers ranging from Jerry Lorenzo to Mike Amiri.

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In 1986, the world was introduced to Ferris Bueller. A breakout role for star Matthew Broderick, the film not only propelled the actor to international fame but marked a departure for director John Hughes. As opposed to Hughes’ numerous other '80s high school romps, Ferris Bueller’s Day Off predominantly focuses on a kid that, for the most part, lacks any serious issues. Bueller is the most popular, beloved, intelligent and successful kid in school. He has a gorgeous girlfriend, a fiercely loyal best friend and seemingly solves any problem that crosses his path.

The film itself simply follows Bueller when he makes the decision to skip school for a much deserved “day off”—he famously quips, “How could I possibly be expected to handle school on a day like this?” Though a nosy principal is on his tail and Bueller and company have a number of near run-ins with his father, the majority of the film the audience watches Bueller’s amazing journey through Chicago unfold—baseball game, high-powered lunch, parade performance and vintage 1961 Ferrari 250 GT California included.

Of Bueller’s many admirable qualities, a key point early on in the film is his sense of style. Vintage Ray-Bans, leopard print sweater vest and leather racing jacket all allude to a young man with a clear sense of history (and taste). Even Bueller’s driving cap somehow feels on trend! While other characters including Bueller’s sister (Jennifer Grey) and girlfriend Sloane (Mia Sara) are typical '80s stereotypes, Bueller’s wardrobe clearly indicates he’s someone special. Today, the film is an undeniable cult classic and, much like the movie itself, Bueller’s look still holds up.

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After nearly six years as the “Fresh Prince”, TV’s most popular high school student was bound for big screen success. While Will Smith took a number of bit parts and supporting roles throughout the filming of The Fresh Prince of Bel-Air, Bad Boys was his first monster blockbuster.

Released in 1995, the Michael Bay-directed film was the first time Smith and co-star Martin Lawrence connected on-screen, and honestly, the critical response was not great. That said, this being a Michael Bay action film, who really cares? In the 25 years since, Bad Boys has transformed into a beloved cult classic, a gem in the buddy cop genre featuring a ruthless criminal, gun fights and car chases galore. Lacking as far as plot is concerned, the film is saved by Smith and Lawrence’s on-screen chemistry, clever back-and-forth banter which is still at points laugh out loud funny. Iconic lines—”Put the gun down and get me a pack of tropical fruit Bubbalicious”—an incredible soundtrack filled with '90s hip-hop standards and Smith and Lawrence at the top of their game make Bad Boys a cult classic.

Insofar as style inspiration, Smith’s Mike Lowry is the clear winner. Despite being a cop, Lowry comes from serious money, and has the wardrobe—and vehicles—to match. Silk shirts, designer sunglasses, sheer tops and Italian loafers all point to peak '90s elegance with a distinct Miami flair (where the film takes place), and look even better next to his Porsche Turbo. Lowry’s wardrobe is a repeating motif in the film, a constant source of amusement for Marcus Burnett (Martin Lawrence), who never passes up an opportunity to mock Lowry’s inherited wealth and bourgeois taste or, in one standout scene, wear his silk shirt to work. Beyond car chases and scene stealing one-liners, Bad Boys has a wealth of style inspiration, making it well worth revisiting.

When Fight Club first released in 1999, reactions were mixed to say the least. While studio executives loathed the film—even augmenting the marketing strategy in order to reduce predicted losses—many critics felt it was one of the most prescient critiques of 20th century consumerism in years.

Adapted from celebrated author Chuck Palahniuk’s novel of the same name, the film focuses around an unnamed narrator (Edward Norton), an insomniac whose life takes a turn following a run in with Tyler Durden (Brad Pitt), an unhinged idealist who rejects modern capitalism and society in a way the narrator only dreams of. After his apartment “randomly” explodes, the narrator meets with Durden at a bar, and on the way out the two agree to fight in the parking lot. Realizing the cathartic nature of brawling for the sheer purpose of feeling something, the two form “Fight Club” (hence the title), which despite its infamous rules—”The first rule of Fight Club is: You do not talk about Fight Club. The second rule of Fight Club is: You do not talk about Fight Club”—rapidly increases in popularity, with similar clubs forming across the country which, eventually, evolve into a movement the narrator could have never imagined.

Unlike the narrator, who wears a Men’s Warehouse-esque suit typical of '90s cubicle drones, Durden’s—a foil in more ways than one—wardrobe is a direct reflection of his anarchist attitude. While he rarely wears a shirt, when he does manage to get dressed Durden opts for outlandish Hawaiian-print button-ups, slim biker jeans and his unforgettable red leather jacket. A soap manufacturer who lives in a dilapidated building and steals rancid animal fat to make his products, Durden’s entire persona is the antithesis of the narrator’s blue collar straight-laced existence. Durden is handsome, driven, idealistic and inspires others, all attributes the narrator desperately wishes he possessed. Durden’s revolutionary world view is not only exemplified through his actions, but in fight sequences and his wardrobe as well.

While Pitt had already established himself as a notable actor throughout the mid- to late-'90s, Fight Club ushered in a new level of fame. Despite underperforming at the box office, unprecedented DVD sales helped Fight Club become a cult classic, with Pitt’s herculean Durden viewed as an ideal male archetype for the new millennium. Durden’s persona—not to mention his look—became ingrained in pop culture history, largely due to Pitt’s spot on performance.

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Following a string of forgettable performances, Reeves reclaimed A-List status with 2014’s John Wick. An unexpected blockbuster success, the film spawned a trilogy where Reeves—as the titular Jonathan (John) Wick—re-enters the world of professional assassins one brutal murder at a time. Operating under the codename “Baba Yaga,” John kills countless men throughout the three films in increasingly inventive, gory and satisfyingly garish ways.

Positioned as a ruthless foil to James Bond, John Wick—in his dark, sharply tailored bulletproof suits—employs the sort of badass machismo that Liam Neeson used to great effect as Bryan Mills in Taken, albeit much better dressed. With the help of famed tailor Luca Mosca, whose previous creds include dressing both Harrison Ford and Gary Oldman, Reeves' made-to-measure suits (which he now wears off-screen as well, paired with hiking boots, no less), have helped transform the 54-year-old actor into a perennial star of GQ’s best dressed list.

While the first two installments were relatively modest films, John Wick: Chapter 3 - Parabellum is a monster, with a studio budget to prove it. The film that finally dethroned Avengers: Endgame at the box office following a literal months-long run, the $75 million film was a box office smash, and finally saw Reeves hop back on a motorcycle on screen—something the actor hadn’t done in earnest since Matrix: Revolutions.

As for wardrobe specifics, Wick wears both black and charcoal three-piece suits with tonal shirts and ties. The effect is more super villain than James Bond, the dark color palette a reflection of the character’s ruthless nature. Yes, for the most part the black dress shirt should be avoided at all costs. But when you’re John Wick—or look like Reeves—you can get away with it.

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Jonah Hill’s directorial debut was a film festival darling. Following protagonist Stevie aka “Sunburn” (Sunny Suljic), the movie—like its title implies—is an exploration of growing up in the mid-'90s and the music, style and subculture that came along with it.

Predominantly focused on skating and its associated lifestyle, relative loner Sunny strikes up a friendship with a local skate crew who drastically change his life when they adopt him into their makeshift brotherhood. Through the course of the film Sunny begins distancing himself from his single mother and abusive old brother, preferring to experiment with alcohol, drugs and party with his crew. His string of increasingly reckless behavior eventually comes to a head during the film's climax, providing an incredibly accurate depiction of what growing up in Southern California was like for lower middle class kids with little supervision.

While the core cast is teens who primarily wear two-sizes-too-large T-shirts and baggy Levi’s, the film’s attention to detail is immaculate. Hill—who actually worked in a skate shop not unlike the one in the film and partially based Sunny on himself—ensured that each T-shirt, hoodie and sneaker was an accurate reflection of what skaters actually wore in 1996. From Emerica sneakers to Zero and Flip T-shirts, each skater is dressed in classic skate gear—the very same that laid the foundation for modern streetwear and continues to inspire everyone from Virgil Abloh to Raf Simons. By the end of the film, even those with zero interest in either skating or the time period will feel the nostalgia, which is exactly what Hill set out to do.

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Much more than a simple high school romance, 10 Things I Hate About You introduced the world to three household names: Joseph Gordon-Levitt, Julia Stiles and, most importantly, the late Heath Ledger. Ledger’s first major role outside of Australia, the film was a critical and commercial success, and kicked off a string of hits for the Australian heartthrob.

Taking place primarily in the Seattle area, the film begins when Cameron James (Gordon-Levitt) moves to town and is immediately smitten with Bianca Stratford (Larisa Oleynik). When Bianca’s overprotective father decides Bianca is only allowed to date when her antisocial older sister Kat (Julia Stiles) begins to do so, James pays bad boy Patrick Verona (Ledger) to seduce Kat and, naturally, drama ensues. Rather than stick with classic '90s cliches, the film has surprising depth and complex characters with rich backstories and real ambition.

Actually a modern retelling of William Shakespeare’s Taming of the Shrew, the hidden literary source material separates the film from its peers, another reason that despite releasing over two decades ago still stands out.

While nerdy James has a couple of great patterned shirts and Kat is to this day a late-’90s fashion favorite, just like his performance it is Ledger’s Verona that steals the show. In slim black boot cut jeans, cowboy boots, short-sleeve button ups and blazers Verona personifies the bad boy trope. But, given that this is the Pacific Northwest, heavy shackets and bombers alongside a shaggy man bun add to the crunchy granola aesthetic. Verona’s standout look, though, is no doubt during prom where he wears a tuxedo any man would be proud of. Overall, Verona does a post-Cobain Seattle proud and, though not his most notable role it’s pretty impressive seeing how even this early in his career Ledger steals the show.

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