33 Stylish Movies EVERY Man Should See

With our current global climate and our orders to quarantine ourselves, now is the perfect time to make a list of stylish movies every man should see.

33 Stylish Movies EVERY Man Should See

The best part?

You can stream all of these from the safety of your home!

So, kick back, grab some popcorn, grab a drink and start bingeing!

Here are the 33 stylish movies every man should see!


Click Here To Watch The Video – 33 Stylish Movies You Need To Watch On Amazon & Netflix


1. The Thomas Crown Affair (1968)

thomas crown affair

The original Thomas Crown (Steve McQueen) sports many different outfits throughout the film and all of them are worn flawlessly. From three-piece suits to sweaters under a classic Harrington jacket, every outfit is a master class. McQueen even has his accessories done right with the iconic pair of Persol’s 714 model sunglasses and a gold Cartier Tank Americanine wrist watch.

The Thomas Crown Affair can be rented on Amazon Prime for $2.99!


2. North by Northwest (1959)

north by northwest movie

Cary Grant’s most iconic film also boasts a very stylish wardrobe. Grant’s classic grey-blue glen check suit is worn throughout. Grant’s suit has been named “the greatest suit in film history” many times and is required viewing for any man who wants to be stylish.

North by Northwest can be rented on Amazon Prime for $3.99!


3. The James Bond Saga (1962-2020)

james bond 007 movies

I mean it’s James Bond. Need we say anything else? From 1962 to today, Bond has been a style icon through it all. From dinner jackets to polo shirts, 007 has worn it all. Some notable movies to check out for sure include: From Russia with Love, Thunderball, On Her Majesty’s Secret Service, Live and Let Die, The World is Not Enough and Casino Royale.

All of Pierce Brosnan’s Bond movies are available to stream on Netflix with a subscription.

The rest of the 007 movies can be found on Amazon Prime video for very cheap by searching James Bond under “Prime Videos.”


4. A Single Man (2009)

a single man movie

Tom Ford’s directorial debut, A Single Man stars Colin Firth as a professor coping with the loss of a loved one. Firth wears a very nice brown suit with a white oxford shirt, tie bar, and thick black glasses through much of the film. Firth brings a whole new meaning to the idea of an everyday suit. With classic 60’s styling and a classic suit template, Firth shows us exactly how to wear a suit and makes it look effortless.

A Single Man is available to stream on Netflix with a subscription!


5. Drive (2011)

drive movie

Ryan Gosling oozes cool as he is the silent-strong type driver in this film. Gosling rocks a white bomber jacket with a scorpion on the back as well as a double denim outfit.

Drive is currently available on Netflix with a subscription!


6. Bullitt (1968)

bullitt movie

Another classic from McQueen, this film sees McQueen sporting an iconic brown tweed jacket and navy turtleneck with charcoal trousers and “playboy” chukka boots. McQueen also wears a maroon shawl collared cardigan with light colored chinos as well.

Bullitt is available to stream on Amazon Prime Video for $2.99 right here!


7. Breathless (1961)

breathless movie

This film has been credited with starting the “French New Wave” of cinema that took over the United States’ popular culture in the 60s. Jean-Paul Belmondo wears an amazing light-colored blazer throughout the film and is a master class on spezzato.

Breathless can be streamed on Netflix with a subscription!


8. The Godfather, Part II (1974)

the godfather part II movie

Covering almost 60 years of style, part II of this amazing trilogy has so many different outfits that are timeless. From Michael Colerone’s grey dupioni silk suit to his tan-cream glen check suit with a cravat and even Vito Corleone’s brown pinstripe suit, there are so many outfits and styles to look at and take inspiration from.

The Godfather, Part II is available to stream on Amazon Prime Video for only $3.99!


9. The Wild One (1953)

the wild one movie

The leather biker jacket. This is the film. Marlon Brando shows how to wear this timeless jacket the correct way.

The Wild One is available on Amazon Prime to rent for $3.99!


10. The Kingsman Movies (2015, 2017)

kingsman movie I and II

Of course, the two Kingsman films had to show up on this list! The Kingsman shows us exactly how to style a double-breasted suit jacket. This is a style move not many make today but one that will instantly set you apart from everyone else.

Both Kingsman movies can be rented for $3.99 each on Amazon Prime Video.

Kingsman: The Secret Service is available here!

Kingsman: The Golden Circle is available here!


11. Rebel Without a Cause (1955)

rebel without a cause movie

James Dean. No not the sausage maker! The actor! A short but bright career, James Dean starred in this classic film and coming of age story. Dean rocks a classic red windbreaker and jeans. He also rocked a crisp white crew neck t-shirt and black boots. This classic bad boy look was how Dean became famous and is a look that any man can pull off.

Rebel Without a Cause is available on Amazon Prime Video for $3.99!


12. Once Upon a Time in Hollywood (2019)

once upon a time in hollywood

This recent film about the death of old school Hollywood has so much style to mine from it. We choose to spotlight Cliff Booth and his aloha shirt and jeans look. Brad Pitt stars as the rough and tough Booth. His outfit throughout much of the film consists of a short sleeved yellow aloha shirt, a white Champion t-shirt, a pair of classic blue jeans and a pair of brown moccasin boots. He also wears a great pair of aviators with a brown lens and a gold rim.

Once Upon a Time in Hollywood is available on Amazon Prime Video for $2.99!


13. 8 ½ (1963)

8 and a half movie

Marcello Mastroianni stars in this French film about an Italian film director who suffers from stifled creativity while filming another film. Mastroianni gives us all a lesson on how to style a monochromatic suit. In all black other than the crisp white shirt, Mastroianni looks amazing throughout the film. He also rocks a classic pair of square glasses which has become very famous in menswear today.

8 ½ is currently available on Hulu with a subscription!


14. Wall Street (1987)

wall street movie

Michael Douglas as Gordon Gekko in Wall Street struck a chord with many and went on to be a style icon through-out much of the 90’s for businessmen. Strong contrasts, expensive accessories, bold colors and pinstripes, Gekko’s style is a classic. Some outfits look slightly dated but there are many details and concepts you can take from his style and modernize them for today.

Wall Street is available to stream on Amazon Prime Video for $3.99!


15. Ocean’s 11, 12 & 13 (2001, 2004, 2007)

oceans 11 12 13 14 movie

The Ocean’s trilogy is a catchall for men’s style. Whether you prefer George Clooney’s classic suit style, Brad Pitt’s gigolo-esque suit style, Matt Damon’s light jackets or Don Cheadle and Elliott Gould’s more outlandish style, there is something for everyone.

Ocean’s 11 is available to stream on Amazon Prime Video for $3.99!

Ocean’s 12 is available to stream on Amazon Prime Video for $2.99!

Ocean’s 13 is available to stream on Amazon Prime Video for $2.99!


16. The Nice Guys (2016)

the nice guys movie

The 1970’s done the right way. While the style in this film is very 70’s and would make Tom Ford very happy, there are many great outfit ideas and concepts to take away from this film. Gosling makes every outfit he wears look amazing. Experiment with colors and patterns as he does in his suits and shirts throughout the film.

The Nice Guys is available to stream on Hulu!


17. Casablanca (1942)

casablanca movie

Of all the ivory dinner jackets to pick, Humphrey Bogart does it effortlessly. An ivory double-breasted dinner jacket with black trousers and a white dress shirt and a black silk bow tie, Bogart is the golden standard when it comes to this look. It is timeless and will always remain an elegant look for gentlemen to be inspired by.

Casablanca is available to stream on Amazon Prime Video for $1.99!


18. Crazy, Stupid, Love (2011)

crazy stupid love movie

Ryan Gosling again shows all of us how to properly dress for any occasion. Whether it is out to the club, out on a date or hanging around home, gosling looks amazing throughout. Ryan Carrell learns from him in the movie when it comes to style and we all can too. I already even reacted to Crazy, Stupid, Love here! Remember, get rid of those 407’s and be better than the Gap!

Crazy, Stupid, Love is available to stream on Hulu!


19. The Man from U.N.C.L.E. (2015)

the man from u.n.c.l.e movie

Starring Henry Cavill and Armie Hammer, 2015’s The Man from UNCLE is an extremely stylish movie in both how it is filmed and what the characters are wearing. Cavil wears almost exclusively suits throughout the film while Hammer’s character has a more casual sense of style. Either way, you get the best of both worlds with this film. A particular shout out to Hammer’s suede jacket and Cavil’s tailor throughout the entire film.

The Man from U.N.C.L.E. is available to stream on Amazon Prime Video for $1.99!


20. American Psycho (2000)

american psycho movie

Patrick Bateman’s style is probably the only thing you want to emulate from this film. Following in the footsteps of Gordon Gekko, he uses bold patterns and contrasts in his suits and shirts. A particular stand out is the charcoal pinstripe flannel suit he wears. It is double-breasted with peak lapels. He also wears a blue dress shirt with a white contrast collar. A contrasting collar is a next level style move that you should try!

American Psycho is available to stream on Hulu!


21. Reservoir Dogs (1992)

reservoir dogs movie

Tarantino’s first film shows us again how great a classic dark suit and tie with white shirt can look. Even one of the “dogs” looks great in their black suits. Even if you are fair-complected, you will always look cool as hell in a black suit and tie.

Reservoir Dogs is available to stream on Hulu!


22. To Catch a Thief (1955)

to catch a thief movie

Another film starring Cary Grant, this film shows off more of his casual style. His navy striped long sleeved jersey with grey trousers is a particular standout in the film. He even wears a red neckerchief with this outfit. If I am being honest, every outfit looks great on Grant in the film!

To Catch a Thief is available to stream on Amazon Prime Video!


23. The Great Gatsby (2013)

the great gasby movie

Leonard DiCaprio played the titular character of Gatsby and he sports some amazing tailoring with very bold colors. From a pink suit to a cream suit to a very nice sweater with linen trousers, Gatsby remains a style icon for men to be inspired by.

The Great Gatsby is available to stream on Amazon Prime Video for $3.99!


24. Three Days in the Condor (1975)

three days in the condor movie

Robert Redford shows all of us how to wear a tweed jacket with a dress shirt and tie. He sports a black and with herringbone tweed sports jacket with a blue chambray shirt and dark navy pants. Redford also wears a dark navy wool pea coat. This pea coat is a classic men’s style staple and looks amazing on Redford.

Three Days in the Condor is available to stream on Amazon Prime Video!


25. Shaft (1971, 2000, 2019)

shaft movie

Shaft played by Richard Roundtree shows us how to pull off a leather trench coat. This is not something you see every day. Shaft wears his brown leather trench coat over a brown plaid flannel suit and a tan turtleneck. This is also a look that would continue to be synonymous with the role of Shaft played later by Samuel L. Jackson.

Shaft (1971) is available to stream on Amazon Prime Video for $1.99!

Shaft (2000) is available to stream on Amazon Prime Video for $3.99!

Shaft (2019) is available to stream on Hulu!


26. Risky Business (1983)

risky business movie

Tom Cruise and Ray-Ban Wayfarer. I mean come on! Cruise wears this classic pair of shades throughout the film putting Ray-Ban on the map. Cruise also shows us all how to style a t-shirt under a blazer without looking like a slob.

Risky Business is available to stream on Amazon Prime Video for $3.99!


27. La La Land (2016)

la la land movie

Gosling strikes again. This time Gosling wears a lot of vintage pieces from his jackets and dress shoes to his Cuban shirts to even his vintage watch. Gosling makes a case for thrift shopping and how some styles will never go out of style.

La La Land is available to stream on Amazon Prime Video for $1.99!


28. Call Me by Your Name (2017)

call me by your name movie

Your step-by-step guide for warm weather outfits, Armie Hammer and Timothee Chalamet show you exactly how to stay stylish in the heat. Hammer sports some great short-sleeved oxford shirts with shorts and loafers. He also wears a pair of Persol 649’s sunglasses. Chalamet shows us how to use bold patterns with his shorts and shirts throughout the film as well. This is a summer style tutorial.

Call Me by Your Name is available to stream on Amazon Prime Video for $3.99!


29. Blade Runner & Blade Runner 2049 (1982, 2017)

blade runner 2049 movie

A classic trench coat will never go out of style. Even in post-apocalyptic 2049. Harrison Ford showed us just how classic a well-tailored trench coat is and went on to spark the cyberpunk trend. Ryan Gosling continues this trend in the sequel and shows us again how cool a trench coat can really be. Take notes on their trench coat to inspire your own!

Blade Runner is available to stream on Netflix!

Blade Runner 2049 is available to stream on Amazon Prime Video for $3.99!


30. Baby Driver (2017)

baby driver movie

Ansel Elgort being an amazing getaway driver wearing a bomber jacket with contrasting sleeves? Jon Hamm wearing a classic black trench coat? Jamie Foxx wearing outlandishly colorful outfits? Yes, there is all that and more in this film – there's something for everyone!

Baby Driver is available to stream on Amazon Prime Video for $3.99!


31. Lethal Weapon 2 (1989)

lethal weapon 1 and 2 movie

The classic buddy cop movie from the 80’s, Mel Gibson’s Martin Riggs character shows us how to style a sportier look. Wearing a letterman jacket, blue jeans and cowboy boots, this style is iconic. Maybe skip the mullet though.

Lethal Weapon 2 is available to stream for free on VUDU!


32. Indiana Jones and the Last Crusade (1989)

indiana jones movie

Away from Indiana Jones’ classic outfit, he wears a very fetching tweed suit while in Paris and shows all of us how to wear a fedora without looking like a complete nerd. Also, there is that classic leather jacket we all know.

Indiana Jones and the Last Crusade is available to stream on Netflix!


33. Mission Impossible: Fallout (2018)

mission impossible fallout movie

Tom Cruise’s latest Mission Impossible shows Ethan Hunt wearing many different outfits with light jackets. This includes a navy-blue leather jacket, a navy suede jacket and a black denim trucker jacket just to name a few. He also wears a very nice suit in the beginning of the film.

Mission Impossible: Fallout is available to stream on Hulu!


And there you go! 33 of the most stylish films that EVERY stylish man must watch!

This should keep you occupied and motivated to plan out your outfits for the future!

The post 33 Stylish Movies EVERY Man Should See appeared first on Real Men Real Style.