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 Palahnuik’s novel of the same name, the film focuses around an unnamed narrator (Edward Norton), an insomniac who lives an aimless life as an automobile recall specialist. The narrator’s life takes a drastic turn when he has a run in with Tyler Durden (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 it’s 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 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 narrators 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.

Guy Ritchie films tend to be polemic. While some see the unorthodox British director as unapproachable, others feel the gritty nature, dark humour and hectic plot as a breath of fresh air in the frankly tired “con” genre. Still, his films tend to be structurally very similar, and his first domestic success was widely criticized for being nearly identical to his debut film, Lock, Stock and Two Smoking Barrels. Focused around a varied ensemble cast in the seedy back streets of London, Snatch traces the intertwining stories of thieves, gangsters, grifters and black market jewelers all with their own personal motives and ambitions. While there is no clear lead, Mickey O’Neil (Pitt) is clearly the films emotional center. An Irish immigrant and legendary bare-knuckle boxer, O’Neil embroils himself in an underground boxing league when he inadvertently knocks out “Gorgeous George.” Asked to fight in George’s place at the behest of bookie Turkish and mob boss Brick Top—with the added caveat of throwing the fight in the 4th round—O’neil instead knocks out his competition in one punch, prompting him to find a solution or risk both his and his fellow immigrant’s lives. While critical reception was predominantly positive, Pitt’s performance was mixed. Although some praised him as the film’s clear through line, his Irish accent was overwhelmingly criticized, with various critics remarking that they simply couldn’t understand a word he says. As far as his wardrobe is concerned though, Snatch is spot on. While the thin brim fedora is clearly dated, Pitt wears it with aplomb, alongside striped shirts, leather jackets, plenty of gold jewelry and an unforgettable shearling coat. Despite his meager financial situation and vagrant status, O’Neil’s clothing reflects a man who values looking presentable, fitting of a back alley boxing legend. In retrospect, Snatch proved two things: 1. Pitt in his prime was pure unadulterated badass and 2. he cannot feign an Irish accent to save his life.

While well recognized by 2001, the film the pushed Pitt from A-list Hollywood talent to international superstar was no doubt Ocean’s Eleven. The first of three films in the Ocean’s trilogy, Pitt stars as Rusty Ryan, the second lead to the titular Danny Ocean (George Clooney). Ocean’s right hand man, Ryan oversees operations and (as revealed in the sequel) is the true heart of the team. Whereas Ocean focuses on the big picture, Ryan, as second-in-command, deals with individual personal and orchestrates the heist. Almost exclusively involved in the planning phase, Ryan is most often seen in louche suits, spread collar shirts, dress shoes and almost always with some sort of fast food in hand. While Pitt’s fits in each of the three films are on point, of particular note is the reptile pattern shirt and white suit combo he wears in Las Vegas—where Eleven takes place—which is nearly identical to the sort of broad lapel, garish garments Tom Ford constantly sends down the runway. A handsome and calculated slick talker, Ryan’s penchant for flashy suits and brash behavior contradicts his methodical nature and despite his various predilections he is a crucial component in every heist. Reprising the role twice, the Oceans franchise helped cement Pitt as a world recognized movie star, and an incredibly well dressed on at that.

Flipping the script on the classic spy genre, Mr. and Mrs. Smith centers around the relationship of John (Pitt) and Jane Smith (Angelina Jolie), an ostensibly mundane upper middle class couple whose marriage of “5 or 6” years is suffering. In reality, unbeknownst to one another John and Jane are both contract killers, working at rival agencies and two of the best in their field. When the couple is assigned the same target, they uncover each other’s secret and each spouse is assigned to eliminate the other. While the film received middling reviews, it was a surprise box office smash, largely propelled by action sequences and the undeniable chemistry between Pitt and Jolie—which not only led to financial glory, but a split from Pitt’s first wife Jennifer Aniston and the start of a real life near 13 year romance between the two co-stars. Although the suits aren’t as slick as Oceans, Pitt’s slim frame, see-through sunglasses (worn throughout the film) inspired droves of men to purchase similar models. The final confrontation in a sporting goods store—where John wears a long sleeve thermal, cargo trousers, bulletproof vest and those same sunglasses—is as good an approximation of our current obsession with tactical military style as any. More than just a stylish film oozing with sex appeal, Mr. and Mrs. Smith gave birth to what was for years one of the most powerful couples in Hollywood. That alone makes the film significant. Pitt’s style is just the cherry on top.

Of his more than 80 films, Pitt will readily admit 2007’s The Assasination of Jesse James by the Coward Robert Ford is his favorite. A revisionist history film adapted from Ron Hensen’s novel of the same name, Pitt stars as the notorious outlaw (and eternal symbol of Western cool) Jesse James opposite his eventual killer Robert “Bob” Ford (Casey Affleck). While masquerading as a traditional Western, the film is in fact a slow building period peace, juxtaposing James’ aging machismo against Ford’s obsession and lust for glory. Though Affleck’s performance is what garnered attention—and an Academy Award nomination–Pitt’s style is untouchable. While Wild West outlaws are already incredibly stylish, few legends measure up to James. The historic figure himself was supposedly as dapper as he was handsome, no doubt why Pitt was director Andrew Dominik’s first choice. His all black three-piece suits with double breasted waistcoat, band collar shirt and traditional cowboy boots put even the most affluent cowboys to shame. Although the real life James was in fact a brutal killer and confederate sympathizer, Pitt’s take introduces a new level of dimension, a man who while on the wrong side of the law, still holds values, one that puts family above all else. Even as a stone cold killer, James has an unexpected depth and throughout the film you can’t help admire him for it. In this case clothes may not make the man, but with a get-up this slick, they help.

One of Pitt’s stronger performances, 2008’s The Curious Case of Benjamin Button was an Academy darling that received the full gamut of nominations, winning in two of the 13 categories it was up for. While Pitt failed to receive the Best Actor award—arguably his best chance in his career thus far—both the Art and Costume departments were awarded for their uncanny ability to (without the help of extensive digital de-aging) convincingly make Benjamin Button (Pitt) age backwards. Adapted from F. Scott Fitzgerald’s 1922 short story of the same name, the 2008 film is a more modern interpretation, set nearly a century after the original. Button, who is miraculously born as an 80-year-old man in 1918, ages in reverse and the story follows his trials and tribulations dealing with a world where he doesn’t truly belong. His love interest, Daisy (Cate Blanchett), is just 7 years old when they first meet, however as their ages grow closer they fall more and more in love, knowing full well that Button’s condition prevents them from ever truly being together. As a young (well, old) man, Pitt dresses like a proper 1920's gentlemen, in full waistcoat and top hat. Eventually, a now middle-aged Button leaves his hometown and finds work on a tug boat, whose captain enlists the ship as a Navy vessel following the attack on Pearl Harbor. Button goes on to win many accolades during his stint in the Navy and after retiring returns home to marry Daisy. The couple conceives a child, however both eventually decide its best if Button leaves due to his condition. It's this middle section of the film where Pitt truly shines, in a perfect leather motorcycle coat resembling those Schott and Belstaff made famous throughout the '50s. Riding a picturesque 101 Scout Indian motorcycle, Pitt is in the prime of his youth, yet still solemn, knowing full well he will soon lose it all. More than a heartfelt story, The Curious Case of Benjamin Button shows how a costume, art and visual department are critical in bringing a film to life. In the case of Button, they made Pitt look exactly how he should at every stage of his inverted life—and it's perfect.

Director Quentin Tarantino’s sixth film—his first with Pitt—is after Django Unchained his most commercially successful (and for many, approachable). An alternate history World War II film, the film focuses on two separate yet intertwining (and ultimately successful) attempts to assassinate Adolf Hitler. While one plot focuses on Shoshana, (Melanie Laurent) a runaway Jewish orphan masquerading as a French cinema house owner, the other focuses on the First Special Service Force (aka the “Basterds), a military militia group comprised of elite Jewish-American soldiers who throw German troops in disarray through sheer violence and brutality—scalping Nazi’s in particular. The force is led but Lieutenant Aldo “The Apache” Raine (Pitt), a former moonshiner who made a name for himself by fighting the KKK in his native Missouri. Clearly a Southern boy at heart, Raine abides by a strict moral code, trusting his soldiers above all else. While his uniform is as classic an example of mid-century military style as any, the look that steals the film is Raine’s white tuxedo jacket worn during the film premiere in the penultimate chapter that would give Daniel Craig’s Bond a run for his money. While the true star of the film is Christoph Waltz’s Colonel Hans Landa, Raine acts as both an agent of change while adding much needed comic relief. Everyone loves a great tuxedo scene, and Raine’s is all time. As Raine exclaims in the final scene, “this just might be my masterpiece.”

First things first: The Counselor is not a great film. While a small minority argue it’s (albeit inadvertently) brilliant, the strong majority believes this is director Ridley Scott’s worst movie. It’s long, violent, cold and dissatisfying‚ but by god is it stylish. Scott has always had a penchant for beautiful costume design, even hiring Craig Green to consult for Alient: Covenant, and The Counselor is no exception. From Reiner (Javiar Bardem) dripping in Versace silk to Malkina (Cameron Diaz) in full St. Barthes beach garb and even The Counselor (Michael Fassbender) in Italian tailoring, wardrobe is a critical component of the film. Westray (Pitt), however, takes the cake. A businessman based in Texas, his tailoring lands somewhere between Tom Ford and Kid Rock, with cropped and embroidered white dinner jackets, huge cowboy hats, and an incredible brown and yellow Western suit—a look that steals the film. Though Westray is brutally murdered (like most of the film’s characters), Pitt’s charm, wit and wardrobe are one of the film’s few redeeming qualities. Even when he makes poor film choices, Pitt still delivers, and Westray is definitive proof as such. That’s what happens when you’re one of the biggest stars in the business.