Before DiCaprio achieved international stardom in Titanic and director Baz Luhrman became a household name with his smash hit Moulin Rouge!, the two paired up for Romeo + Juliet. Billed as Shakespeare for the MTV generation, the relatively small budget film ($14.5 million) reimagined the classic tale of star-crossed lovers in turn-of-the-century Verona City, an amalgam of Los Angeles, Miami and Mexico City (where principal shooting occurred). While a modern reinterpretation, Luhrman insisted the film stay true to the original text, offering a stark juxtaposition of 16th Century idioms and modern sensibilities. Rather than royals, the feuding Montagues and Capulets were warring crime families—the former resembling the Irish mob while the latter was loosely based off Hispanic street gangs and the Mexican cartel. While today Luhrman’s visual language is his trademark, back then, few knew the director’s obsessive attention to detail, saturated color pallette and predilection for top-notch costume design. Working alongside celebrated costume designer Kym Barret (The Matrix trilogy, Aquaman), Lurhman ensured that the family figureheads were all clad in period correct power suiting—courtesy of Yves Saint Laurent by Tom Ford—while the rebellious younger generation wore looks more emblematic of their constant infighting including custom DG by Dolce & Gabbana kevlar vest for the Capulets and custom printed Hawaiian shirts and BDU cargo pants for the New Wave Montagues. As the lead, particular attention is paid to Romeo’s wardrobe, from the disheveled tuxedo in the opening scene to the custom made Prada wedding suit designed by Miuccia Prada herself specifically for the role. More than just establish DiCaprio as a lustworthy leading man, the film became a mood board for all things ’90s, from oversized suiting to excessive teen angst. Even 20-plus years later, few films rival Romeo + Juliet’s style, and as its leading man, DiCaprio never disappoints.

DiCaprio’s first picture with director Martin Scorcesse would set off one of the actor’s decade-spanning actor-director partnerships; the duo reunited for The Aviator and The Departed. Unlike The Departed, whose thick undercover cops-vs.-Irish mob drama has DiCaprio appearing in grungy, unremarkable street clothes, it’s Gangs of New York that oozes with style—especially when it comes to recreating the unique look and feel of each faction. Of course DiCaprio’s turn as Amerstdam Vallon would be one of, ultimately, many times DiCaprio would head into the late-19th and early-20th centuries. Given Vallon’s position as the orphaned son of a Dead Rabbits gang leader—combined with its 1860s setting—DiCaprio’s style here is tattered and dishelved; given the cramped nature of immigrant communities in New York City at the turn of the 20th century, this stands to reason. Vallon’s appearance is all the more apparent, especially when stacked against his nativist nemsis, Bill the Butcher (played by Daniel Day-Lewis). While Vallon’s look resembles a blend that modern fashion fans might describe as a blend of Engineered Garments, Kapital, Junya Watanabe, Paul Harnden Shoemakers and Geoffrey B. Small, Bill the Butcher appears damn near dandyish—a fitting cover for the violent nature that lurks slightly below the surface. While this movie is set in a much more chaotic and malleable form of New York City (long before anything remotely close to “fashion week” was even conceived) it’s interesting to think that—even in that bygone era—people were still relying on fashion to identify with and establish their own tribes on the streets of NYC.

For nearly 17 years, the story of the infamous check forger turned FBI agent Frank Abagnale Jr. sat in production in limbo. When Spielburg acquired the rights, however, after bouncing between a number of notable directors he finally decided to helm the film himself. Already an international superstar following Titanic, DiCaprio’s slick charm and seeming inability to age made him the perfect candidate to portray the 17-year-old world-class grifter. Set in 1963, Catch Me If You Can follows Abagnale’s rise from lowly con man to world class bank thief, impersonator, prisoner and finally FBI employee. Spielberg and DiCaprio’s first—and as of yet only—film together, the two brought Abagnale to life through a lights out performance and an incredible attention to detail. Period correct set pieces, automobiles, idioms and wardrobe all make the film—and Abagnale—feel all the more believable. While Abagnale begins life as relatively poor high school drop out, after masquerading as an airline pilot he (literally) changes his entire persona. A captain during Pan American Airlines’ heyday, Abagnale is dapper as can be in the custom made double breasted pilot’s uniform. As his schemes grow increasingly large, so do his outfits, with imported Italian tailoring, designer tortoiseshell frames and handmade Oxfords all showcasing both wallet and taste level. Then there’s the unforgettable wedding scene, where Abagnale attempts to flee from the FBI while stuffing thousands of dollars in a Louis Vuitton Presidential briefcase—then a must-have for affluent men of taste. While Abagnale’s luck runs out and he is ultimately caught in his mother’s native Montrichard, France, he looks immaculate all the while.

DiCaprio’s second turn with Scorcesse at the helm netted the actor a Golden Globe, portraying the manic genius of millionaire Howard Hughes. Hughes, a real-life pioneer in both aviation and Hollywood, was wracked by various neuroses (especially Obsessive-Compulsive Disorder) which simultaneously stoked his game-changing ambitions while alienating him professionally, politically and emotionally. Set primarily in the 1930s and 1940s, places DiCaprio in another early-20th century setting, especially as the United States was coming off the chaos of World War II. While Hughes was exceedingly weathly, his personal interests ensured that he spent as much time in practical workwear and flight gear (for the era) as he did in suits and tuxedos. As such, the aesthetic of Hughes wardrobe is a blend of old school-Americana and vintage military style—think A-2 leather flight jackets and trousers tucked into field boots—as well as loose-but-luxurious tailoring—think broad shouldered Italian-style suiting. For those looking to recreate Hughes’ looks from the film, you’d be well suited with pieces from The Real McCoy’s and Tricker’s for the former style, and pieces from Isaia, Brunello Cucinelli and Barena or Ermenegildo Zenga (for something a bit more modern). While The Avaitor walks this duality seamlesslessly as the film follows Hughes life, netting costume designer Sandy Powell an Academy Award. DiCaprio’s ability to portray the two-sided nature of Howard Hughes (fearless-but-anxious) helped cement his reputation as a generational talent; his ability to carry off the two-sides of Hughes’ wardobes (airplane innovator and Hollywood playboy) certainly adds to his history as an on-screen style icon.

It’d be easy to tuck 1997’s Titanic on this list, given the film’s status as one of the most successful blockbusters of all time. But we’d challenge our readers to step back and examine another Leonardo DiCaprio and Kate Winslet-cinematic pairing: 2008’s Revolutionary Road. Set squarely in 1950s Connecicut, Frank and April Wheeler (played by DiCaprio and Winslet respectively) are the pinnacle of the mid-century, post-war American Dream. Under the surface however, their relationship is pure façade, empty and passionless as the cookie-cutter standards of this era in American life. Speaking to Elle, costume designer Albert Wolsky explained, “I had everybody in hats and suits and ties. It created an atmosphere for Leo DiCaprio's character to disappear in this crowd. Many times you can't even find him because he looks like everybody else.” Even though this period of American culture was more about fitting in—seen prominently in shows like Mad Men—Frank Wheeler’s outfits in the film could easily be worn today (without looking like you’ve stepped out of a time warp). To get the obvious period styling out of the way, Frank’s suiting—pleated trousers, soft fedoras, muted grays—are exactly the kind of items a standard-issue businessman would wear with anonymity. It’s in his off hours, seen in scenes at the beach or around the Wheeler’s home on 115 Revolutionary Road, where Frank begins to shine. Colorful and embroidered camp colorshirts (see burnt orange and soft blue) would fit into any modern man’s summer wardrobe. While DiCaprio’s turn as Frank Wheeler serves as a well of inspiration for light summer staples, be warned: Revolutionary Road is easily one of the most intense films on this list.

Though Django Unchained was Quentin Tarantino and DiCaprio’s first joint project, it was not for lack of trying. While traditionally a leading man, Tarantino—as he is wont to do—always saw DiCaprio as an antagonist, originally offering him the role of Hans Landa in Inglorious Bastards, which ultimately went to his Django co-star Christoph Waltz. The two finally managed to come together for Django, where DiCaprio plays suave yet demented plantation owner Calvin Candie. A true businessman and Southern dandie, Candie’s garish appearance provides a stark contrast to his brutal nature, a man who regularly buys slaves for the sole purpose of “Mandingo” fights—undocumented brawls to the death, gruesomely depicted in typical Tarantino fashion. Despite his horrific nature, Candie maintains a calm demeanor as he invites protagonists Dr. King Shultz (Waltz) and the titular Django (Jamie Foxx) to has Candyland estate, where he serves them a lavish dinner and discusses business while smoking from an elongated engraved cigarette holder. Candie’s uniform varies throughout the film from work clothes—a rough wool blazer, striped shirt, chaps and neckerchief—to full on formal attire including a velvet dinner jacket, waistcoat, ascot and embroidered loafers that wouldn’t be out of place in a Tom Ford showroom, but no matter the scene he looks impeccable. What’s truly interesting, though—and unique to Tarantino films—is the depth and dimension DiCaprio brings to the slave trader. Despite being a ruthless, bigoted scumbag, the audience can’t help but keep its eyes on him. There’s something about Candie that’s engaging, Tarantino’s not-so-subtle nod towards the enduring presence of racism in the South. Give it to Tarantino and DiCaprio to make a sociopath look this good.

There’s no debate: The Great Gatsby—as a novel and as a film—is the definition of an “American standard”. Part cultural critique and part romantic drama, it’s damn near impossible to pass through an American middle school, high school or university without encountering F. Scott Fitzgerald’s seminal work. Set during the Jazz Age in the 1920s, the Baz Luhrmann-helmed take on The Great Gatsby received a surprising amount of support from fashion labels to help bring Gatsby’s (and, true to his own aesthetic, Luhrmann’s) ostentatious appearance to life. Brooks Brothers—itself founded in New York as far back as 1818—provided and directly collaborated with costume designer Catherine Martin on all of the suiting for all of the male leads, from DiCaprio’s Jay Gatsby, to Tobey Maguire’s Nick Carraway and Joel Edgerton’s Tom Buchanan. "Fitzgerald was a Brooks Brothers customer," Martin explained to The Hollywood Reporter. "Brooks Brothers is mentioned numerous times in Fitzgerald's writings as a representation of the ultimate gentleman's purveyor of fine clothing." When it comes to Gatsby’s personal style, the 2013 film leans into the character’s love for pushing things over-the-top. While Brooks Brothers is an American tailor through-and-through, Gatsby’s peak lapel pink pinstripe look and bleached out three-piece option bring an Neapolitan flair to the proceedings. Of course, the most memorable look has to be the, now-meme-worthy, tuxedo-clad Gatsby toasting to the camera. It’s not Gatsby’s flashiest look on it’s own, but with Luhrmann’s extravagant (and, some might say, “on the nose”) fireworks display framing the character, it stands as one of the most memorable outfits—if not moments—of the film.

While many films offer depictions of 1980s stockbrokers and their manipulative tactics—Wall Street, Boiler Room, American Psycho, Glengarry Glen Ross and so forth—none do it with the panache of The Wolf of Wall Street. Scorsese and DiCaprio’s fifth outing, The Wolf of Wall Street documents the rise and fall of Jordan Belfort, whose Stratton Oakmont brokerage firm was one of many engaging in stock manipulation, aggressive tactics and outright fraud amidst the ‘80s stock boom. Following the notorious ‘87 stock market crash—aka Black Monday—Belfort, then a struggling young professional with just a Series 7 to his name, finds a job in Long Island pushing penny stocks to middle-class blue collar workers. Realizing the insane commissions on penny stocks, Belfort alongside a number of close friends found Stratton Oakmont, where they begin selling blue chip stocks to upper class individuals alongside more “profitable” penny stocks, reaping in massive profits off their consistent losses. As Belfort’s wealth starts pouring in, his style transforms from Men’s Warehouse to Armani, Valentino and Gucci power suits like many Wall Street contemporaries wore. While stiff collars, pin-striped double-breasted blazers and French blue shirts were gauche even then, this is Dicaprio we’re talking about, who looks as good as anyone can in the prototypical finance get up. Outside the office, Belfort veers between off duty sweatpants and Nike Cortez’s to absolutely monumental boating attire, including an unforgettable scene on his Yacht where Belfort attempts to bribe FBI officers while dressed in a tucked in Polo, white trousers, and Persol sunglasses, casually sipping a chilled red. While the sweatpant, white tee, chambray shirt and Nike Cortez combo Belfort wears as he crashes a picturesque white Lamborghini Countach may be the film’s most memorable scene, Belfort’s yacht fit remains unmatched, and shows that regardless of the era, DiCaprio remains undefeated.