The strongest cinema characters require strong wardrobes to make an impression. So it’s no accident that the most memorable roles from throughout cinema history have been, in Style terms, the really cool movie characters. In films set in the professional world, characters’ fashions reveal not only their occupations, but are freighted with clues as to their attitudes and motivations. And they also radiate back out into the world, creating trends that are driven by audience demands to replicate a particular look. Here are 11 stylishly influential professional workwear looks sported by the most memorable movies characters from the past five decades.

1. Christian Bale as Patrick Bateman

Patrick Bateman, the psychopathic protagonist of American Psycho, sees the world, and everyone in it, through clothes and appearances. Played by Christian Bale in the 2000 film adaptation, Bateman’s wardrobe features Valentino suits, Oliver Peoples glasses and Bottega Veneta shoes. The hyper masculine broad-shouldered suit style popular in the 1980s is synonymous with the character.

2. Sean Connery as James Bond

Thought of by many as the definitive Bond, Sean Connery epitomizes the smooth elegance of Agent 007. The wardrobe for Connery’s Bond films reflects this, with beautifully cut suits featuring such subtle touches as gauntlet cuffs. Most of Connery’s suits were made by famous London tailor Anthony Sinclair, with a looser fit and narrow lapels to suit Connery’s athletic physique. It’s a look that has endured to appeal to all ages.

3. Diane Keaton as Annie Hall

As Woody Allen’s most famous heroine, Annie Hall is characteristically quirky and unconventional, as is her style. Played by Diane Keaton, Hall’s wardrobe was heavily influenced by Keaton’s own tomboyish style, with additional styling by Ruth Morley. Featuring simple shoulder-length hair, men’s tailoring and wide-brimmed hats, the look is truly iconic. Keaton’s look was part of a visual style that endured and even influences best-selling items as incongruous as bedding!

4. Colin Firth as George Falconer

It shouldn’t be surprising that the 1999 film A Single Man directed by legendary fashion designer Tom Ford features an incredibly stylish main character. Colin Firth brings a stylish edge to the leading man role of 1960s college professor, George Falconer. The character’s stand-out looks include a brown suit, thick-framed glasses and a simple tie bar.

5. Richard Roundtree as John Shaft

In the infamous 1970s private-eye film Shaft, and its influence on young African Americans at the turn of the ’70s and throughout the decade, the title role was one of those cool movie characters that truly became an enduring style inspiration. With a look inspired by the beatnik movement and the urban working class, Shaft’s signature look includes a long leather trench coat, turtle neck sweater and flat-fronted straight-leg trousers.

6. Jason Schwartzman as Max Fischer

The kooky prep-school style worn by Rushmore’s main character, Max Fischer, shows that even school uniforms can be made unique. Played by Jason Schwartzman in his first ever role, Max accessorises his navy blazer, red tie, white shirt and beige chinos with a red beret and a plethora of badges from his many extra-curricular activities. Adidas trainers are the only modern touch to his outfit, reminding us that despite his precociousness, he’s still a teenage boy.

7. Meryl Streep as Miranda Priestly

Reportedly inspired by Vogue editor Anna Wintour (see below), Miranda Priestly has a modern era-defining iconic professional look, with a wardrobe that encompasses towering high heels, pencil skirts, fur, snakeskin and luxe accessories. Played by Meryl Streep, Miranda Priestly has a polished appearance that reflects her impenetrable personality—for cool movie characters in Priestly’s case, read ‘terrifying’!

8. Samuel L. Jackson as Jules Winnfield

This movie takes the stylebook of cool movie characters to extremes. In accordance with writer/director Quentin Tarantino’s belief that all professional criminals wear a black suit, white shirt and black tie, Jules Winnfield’s attire in Pulp Fiction is classic and monotone. It’s the accessories that bring the character, played by Samuel L. Jackson, to life. The gold jewellery, jheri-curled hairstyle and intricate facial hair, vividly convey the sense of a man who isn’t scared to stand out, despite his predominantly monochrome colour scheme of choice.

9. Zooey Deschanel as Summer Finn

If any film character acts as an office-working everywoman providing realistic fashion inspiration for the workplace, it’s Summer Finn from 500 Days of Summer. Played by Zooey Deschanel, the character dresses mostly in blue, often sporting pretty retro dresses, hair-bows and embellished cardigans. This creates a low-maintenance look that expertly mixes old and new for an effortless feel.

10. Leonardo DiCaprio as Jay Gatsby

Jay Gatsby is not only one of cinema’s cool movie characters, but also a giant, iconic figure of 20th century fiction. Created by F Scott Fitzgerald, Gatsby is a character who builds his life based on appearances, so it makes sense that his clothes would exude conspicuous elegance. In Baz Luhrmann’s 2013 film, Gatsby, played by Leonardo DiCaprio, doesn’t shy away from accessories and boasts an endless collection of colourful suits. Although his ‘new money’ ostentatiousness gives him away, some of his loudest outfits have created lasting film fashion moments, such as the infamous pink suit derided by supporting character Tom Buchanan.

11. Renée Zellweger as Elle Woods

No film has encapsulated early-Noughties style quite like Legally Blonde. The protagonist, Elle Woods, is a ditzy sorority girl turned serious lawyer. Played by Renée Zellweger, the character sports numerous legendary all-pink outfits, always accessorized with Bruiser, her chihuahua. As the character develops, so does her style, as she manages to incorporate bright pink into a professional workwear wardrobe.

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