The 30 Most Stylish Movies Every Gentleman Must See

Aside from style icons and style blogs, what better way could one get style inspiration and be entertained at the same time, than by watching stylish movies?

Style inspiration comes from the fashion world, daily life, style icons, books, fashion magazines, as well as from stylish movies. So today we have curated a list of most stylish movies that every gentleman should see. I’m talking about the kind of movie that would inspire you to dress well, improve your style, and look classy all the time.

Check out these most stylish movies that will inspire your wardrobe, lifestyle, and everything else organized according to the year of release in descending order.

Enjoy!

30 MOST STYLISH MOVIES EVERY GENTLEMAN MUST SEE

#30. THE GENTLEMEN (2020)
Genre: Action Comedy
Actors: Charlie Hunnam (Ray), Matthew McConaughey (Mickey Pearson), Colin Farrell (Coach), Hugh Grant (Fletcher)
Directed by: Guy Ritchie
Plot Summary:

#29. The Banker (2020)

Two African American entrepreneurs in the 1950s hire a white man to pose as the head of their company while they posed as a janitor and a chauffeur and ran the business.
Initial release: 6 March 2020
Director: George Nolfi

#28. The Irishman (2019)

In the 1950s, truck driver Frank Sheeran gets involved with Russell Bufalino and his Pennsylvania crime family. As Sheeran climbs the ranks to become a top hit man, he also goes to work for Jimmy Hoffa — a powerful Teamster tied to organized crime.
Director: Martin Scorsese
Cast: Robert De Niro as Frank Sheeran
Al Pacino as Jimmy Hoffa
Joe Pesci as Russell Bufalino
Ray Romano as Bill Bufalino

#27. Crazy Rich Asians (2018)

Rachel, a professor, dates a man named Nick and looks forward to meeting his family. However, she is shaken up when she learns that Nick belongs to one of the richest families in the country.
Director: Jon M. Chu

#26. Murder On The Orient Express (2017)

Plot Summary:

A lavish trip through Europe quickly unfolds into a race against time to solve a murder aboard a train. When an avalanche stops the Orient Express dead in its tracks, the world’s greatest detective — Hercule Poirot — arrives to interrogate all passengers and search for clues before the killer can strike again.

Director: Kenneth Branagh
Writers: Michael Green (screenplay by), Agatha Christie (based upon the novel by)
Stars: Kenneth Branagh, Penélope Cruz, Willem Dafoe

24. JOHN WICK: CHAPTER 2 (2017)

Legendary hitman John Wick is forced back out of retirement by a former associate plotting to seize control of a shadowy international assassins’ guild. Bound by a blood oath to help him, John travels to Rome where he squares off against some of the world’s deadliest killers.

2017 | Crime film/Thriller ‧ 2h 2m
IMDb: 8.1/10 | Rotten Tomatoes: 90% | Metacritic: 75%
Initial release: 30 January 2017 (Los Angeles)
Director: Chad Stahelski
Stars: Keanu Reeves, Riccardo Scamarcio, Ian McShane

#22. THE MAN FROM U.N.C.L.E. (2015)

Genre: Action, Comedy
Director: Guy Ritchie
Writers: Guy Ritchie (screenplay), Lionel Wigram (screenplay)
Stars: Henry Cavill, Armie Hammer, Alicia Vikander

Plot Summary:

In the early 1960s, CIA agent Napoleon Solo and KGB operative Illya Kuryakin participate in a joint mission against a mysterious criminal organization, which is working to proliferate nuclear weapons.

#21. KINGSMAN: THE SECRET SERVICE (2014/2015)

Genre: Action, Adventure, Comedy
Actors: Colin Firth, Taron Egerton, Samuel L. Jackson
Director: Matthew Vaughn
Plot Summary:
A spy organization recruits an unrefined, but promising street kid into the agency’s ultra-competitive training program, just as a global threat emerges from a twisted tech genius.

#20. THE WOLF OF WALL STREET (2013)

Genre: Biography, Comedy, Crime
Actors: Leonardo DiCaprio, Jonah Hill, Margot Robbie
Director: Martin Scorsese
Plot Summary:
In 1987, Jordan Belfort (Leonardo DiCaprio) takes an entry-level job at a Wall Street brokerage firm. By the early 1990s, while still in his 20s, Belfort founds his own firm, Stratton Oakmont.

Together with his trusted lieutenant (Jonah Hill) and a merry band of brokers, Belfort makes a huge fortune by defrauding wealthy investors out of millions. However, while Belfort and his cronies partake in a hedonistic brew of sex, drugs and thrills, the SEC and the FBI close in on his empire of excess.

#19. THE GREAT GATSBY (2013)

Genre: Drama, Romance
Actors: Leonardo DiCaprio, Carey Mulligan, Joel Edgerton
Director: Baz Luhrmann
Plot Summary:
Midwest native Nick Carraway (Tobey Maguire) arrives in 1922 New York in search of the American dream. Nick, a would-be writer, moves in next-door to millionaire Jay Gatsby (Leonardo DiCaprio) and across the bay from his cousin Daisy (Carey Mulligan) and her philandering husband, Tom (Joel Edgerton).

Thus, Nick becomes drawn into the captivating world of the wealthy and — as he bears witness to their illusions and deceits — pens a tale of impossible love, dreams, and tragedy.

#18. SKYFALL (2012)

Genre: Action, Adventure, Thriller
Actors: Daniel Craig, Javier Bardem, Naomie Harris
Directed by: Sam Mendes
Plot Summary:
Bond’s loyalty to M is tested when her past comes back to haunt her. Whilst MI6 comes under attack, 007 must track down and destroy the threat, no matter how personal the cost.

#16. WALL STREET : MONEY NEVER SLEEPS (2010)

Genre: Drama, Thriller , produced in 2010 USA
Actors: Shia LaBeouf, Charlie Sheen, Carey Mulligan, Susan Sarandon
Directed by: Oliver Stone
Plot Summary:
20-plus years after he introduced us to the phrase “greed is good,” controversial filmmaker Oliver Stone (W., World Trade Center) returns to the world of high finance, unfettered capitalism, and white-collar crime. Michael Douglas reprises his Oscar-winning role as Gordon Gekko, the deliciously diabolical money magnate who never passes up a chance to make a buck. Shia LaBeouf also stars as a young trader embroiled in a puzzling murder.

#15. QUANTUM OF SOLACE (2008)

Genre: Action, Hollywood Tone, Thriller
Actors: Daniel Craig, Olga Kurylenko, Mathieu Amalric
Directed by: Marc Forster
Plot Summary:
Following the death of Vesper Lynd, James Bond (Daniel Craig) makes his next mission personal. The hunt for those who blackmailed his lover leads him to ruthless businessman Dominic Greene (Mathieu Amalric), a key player in the organization which coerced Vesper. Bond learns that Greene is plotting to gain total control of a vital natural resource, and he must navigate a minefield of danger and treachery to foil the plan.

#9. HOODLUM (1997)

Genre: Crime, Drama, Period , produced in 1997 USA
Actors: Laurence Fishburne, Andy Garcia, Tim Roth
Directed by: Bill Duke
Plot Summary:
HOODLUM stars Laurence Fishburne in a powerful performance as Ellsworth “Bumpy” Johnson, the notorious Harlem gangster of the 1930s. Director Bill Duke mixes a sumptuous visual style with a message of black empowerment. Bumpy gets out of prison and goes to work for the Harlem numbers powerhouse known as Madam Queen (Cicely Tyson), bringing him into conflict with the psychopathic Dutch Schultz (Tim Roth), who is trying to take over the numbers racket in Harlem. As the blood flows through Harlem streets, those around Bumpy begin to question his methods– and his morals.

#8. CASINO (1995)

Genre: Crime, Drama, Period , produced in 1995 USA, France
Actors: Robert De Niro, Joe Pesci, Sharon Stone, James Woods
Directed by: Martin Scorsese
Plot Summary:
In early-1970s Las Vegas, low-level mobster Sam “Ace” Rothstein (Robert De Niro) gets tapped by his bosses to head the Tangiers Casino. At first, he’s a great success in the job, but over the years, problems with his loose-cannon enforcer Nicky Santoro (Joe Pesci), his ex-hustler wife Ginger (Sharon Stone), her con-artist ex Lester Diamond (James Woods) and a handful of corrupt politicians put Sam in ever-increasing danger. Martin Scorsese directs this adaptation of Nicholas Pileggi’s book.

#7. GOOD FELLAS (1990)

Genre: Crime & Drama
Actors: Ray Liotta, Lorraine Bracco, Robert De Niro, Joe Pesci, Paul Sorvino
Directed by: Martin Scorsese
Plot Summary:
Based on Nicholas Pileggi’s book WISEGUY, Martin Scorsese’s GOODFELLAS is a wry, violent, and exhilarating film about the life of Henry Hill, an aspiring criminal who ends up in the FBI’s witness protection program after testifying against his former partners. As a poor Irish-Italian growing up in 1950s New York City, Hill (Ray Liotta) rises through the ranks of his Brooklyn neighborhood’s organized crime branch, and with money from the mob he begins living the good life, complete with a beautiful bride, Karen (Lorraine Bracco), a fancy house, and the best seats at the most exclusive restaurants.

A botched robbery lands Henry in prison for a brief period of time, and when he gets released, his reckless infidelities and drug abuse damage his association with his adopted family.

#6. THE UNTOUCHABLES (1987)

Genre: Action, Crime, Historical, Hollywood Tone, Period, Thriller
Actors: Robert De Niro, Kevin Costner, Sean Connery
Directed by: Brian De Palma
Plot Summary:
Kevin Costner is idealistic federal agent Eliot Ness, whose assignment to clean up Prohibition-era Chicago leads to violence and manly questions about upholding the law. Initially powerless to stop the flow of booze into the city (the police force is corrupt and everyone in town seems to be on the mob’s payroll), Ness finds guidance from an older streetwise cop (Sean Connery, who won an Academy Award for this role) who convinces him he’ll need to break some rules if he wants to bring down head mobster Al Capone (Robert De Niro). Andy Garcia and Charles Martin Smith play Ness’s other recruits, who together must stand tall against a city full of assassins.

#3. BREAKFAST AT TIFFANY (1961)

Paul is a struggling writer who’s just moved into his new apartment in New York. He comes across Holly, who is a party animal and a socialite. But what lies beneath her beauty is her dark past.

Director: Blake Edwards

#1. LA DOLCE VITA (1960)

In Federico Fellini’s lauded Italian film, restless reporter Marcello Rubini (Marcello Mastroianni) drifts through life in Rome. While Marcello contends with the overdose taken by his girlfriend, Emma (Yvonne Furneaux), he also pursues heiress Maddalena (Anouk Aimée) and movie star Sylvia (Anita Ekberg), embracing a carefree approach to living. Despite his hedonistic attitude, Marcello does have moments of quiet reflection, resulting in an intriguing cinematic character study.

Director: Federico Fellini

FINAL THOUGHTS

I hope you enjoyed our list of Most Stylish Movies. We’ve watched each and every one of them at least twice and would say from firsthand experience that they are all both entertaining and inspiring as far as dressing well is concerned.

Please feel free to drop your comments and contributions in the comment section below and share the story as well. Your feedback helps us improve and serve you better.

If you will like to contact me, send me an email info@kobikoachman.com. You can also find us on Twitter, Instagram, and Facebook. Feel free to join/follow us on any of the channels you frequently use as we continuously inspire you on how to dress well, do well and live well.

Until next time gentlemen – Sayonara!

Yours in Style,

Kobi O. Mbagwu (Mr. Kobi)
Founder, KOBI KOACHMAN
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Mr. Kobi

My name is Kobi O. Mbagwu, a professional image consultant, menswear style expert, and entrepreneur who uses fashion, style and clothing as key tools in transforming ordinary men into extraordinary classy gentlemen. My personal goal is to help gentlemen dress better, live well, do well and develop a unique personal style that matches their lifestyle and goals. I believe that success can be built through style. I believe that fashion is a tool that can be used to change people’s lives positively. I also strongly believe that if you dress well, you look good, and if you look good, you feel good and when you feel good, you worry less, and the less you worry the more you are able to stay motivated and focused on your goals pursuit and by so doing you are able to live a more fulfilling and successful life.

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