Best movies with Style Inspiration for men 2022

best movies with style inspiration for men

If you want to have a larger wardrobe, better fashion sense or just know more about the fashion scene, the best thing you can do is watch movies.
But not just any movie! Some are good for getting an idea of how one should dress in certain situations; some are great for showing iconic outfits that still influence today’s fashion or what you can expect on red carpets. Here are the best movies with Style Inspiration for men.

At The Timeless Gentleman we like our men well dressed and good looking (who doesn’t?), so we thought it would be interesting to make up a list with which every man would ideally see movies. After all, why learn something if there’s no audience watching?

6 best movies with style inspiration for men

There isn’t a ranking system on this list; it must be noted that men’s fashion movies are quite different from men’s style movies, and yet both genres have several differences in relation to men’s clothing.

The men’s fashion genre is more about clothes, with characters that wear specific items that would suit the occasion or even be a portrayal of their personality.

Men’s style movies usually wear iconic pieces that give them a certain aura, but they’re not necessarily suited for the occasion. A good example would be James Bond dressing up in Tom Ford suits while saving the world;. However, we want him to look sharp and professional, he also needs some form of comfort so he can escape any unfavourable situation unscathed!

Just like there isn’t really a ranking system on which movie is better than others, men’s fashion and men’s style movies are appraised in much the same way – one man’s favourite could be another man’s worst nightmare (although we would like to think all men would like a well-made men’s fashion movie).
There is no men’s fashion or men’s style genre as such, but there are better menswear movies than others. We reviewed the best ones, and here are best movies with style inspiration for men:

The Blues Brothers (1980)

best movies with style inspiration for men 2022

Elwood (John Belushi) and Jake Blues (Dan Akroyd) take on Chicago in this 1980 comedy classic. Fashion highlights include: Jake wearing an ‘Al Hirt’ tuxedo with a ruffled shirt, Elwood sporting a sharp three-piece suit with thin tie and two-tone brogues, many men in black suits with matching hats.

The 1980 American musical comedy crime film directed by John Landis is a cult classic, and with good reason: men’s fashion! Belushi and Akroyd wear some iconic menswear outfits that every man would love to have in his wardrobe. The men’s style in this movie can be summarised as ‘simple but elegant and ‘sharp’. This means we see men wearing simple white or blue shirts that are worn underneath dark suits with slim lapels.

Shirt collars are usually spread open at the neck while ties are kept sharp – not too skinny nor too wide. In this movie, men’s style excels when it comes to men’s accessories. The men are often seen with hats – either fedoras or caps – and all men seem to be wearing cuff-links, ties bars and watches. If you can take anything away from this movie, it has to be sunglasses: they’re worn by men whenever the sun is out (which is quite often in Chicago), but never indoors!

The Great Gatsby (2013)

style inspiration in movies menswear

Jay Gatsby (Leonardo DiCaprio) wears a tuxedo with slim lapels; men dance with their jackets unbuttoned; Nick Carraway (Tobey Maguire) wears an orange rollneck sweater over a white shirt; men wear vests under their suit jackets.

Fashion highlights include: men dancing in slim-fit tuxedos with peaked lapels, men wearing vests under their jackets and men in bow ties
The 2013 American romantic drama film directed by Baz Luhrmann is a modern retelling of F. Scott Fitzgerald’s 1925 novel of the same name; it follows the life and times of Jay Gatsby (DiCaprio), a millionaire who throws lavish parties every weekend. In this movie, the men’s fashion turns classic menswear pieces such as suits and hats into something more modern, sleek, and fitted to men’s bodies.

Men wear slim-fit suits that show off their shoulders while keeping everything else neat and tidy – similarly to what we see men wear when attending cocktail parties at DowntonAbbey. Some men are even wearing slim-fit tuxedos with peaked lapels while others wear vests under their suit jackets! Men’s style gets really interesting when men dance, mainly because men take off their suit jackets and dance in shirtsleeves or slim sleeveless vests. Hats – especially fedoras – plus bow ties, gloves and even top hats also feature men’s accessories in this movie to add that extra special touch!

The Great Escape (1963)

best movies about style

Men wear double-breasted suits; men buy clothes at the general store; men wear sunglasses.

Fashion highlights include: men wearing rayon Hawaiian shirts over white tees, men buying clothes at the general store, Steve McQueen wearing a panama hat
The 1963 American World War II epic film directed by John Sturges is a true men’s fashion classic! In the movie, men are digging tunnels, dressing up as German soldiers and killing people. It doesn’t sound all that glamorous, but it sure looks good on men!

Men wear double-breasted wool suits with wide peaked lapels; men buy clothes from the general store where they can get anything they need for their escape – including Hawaiian shirts over white tees, men wearing sunglasses at night under a cap and men wearing panama hats to keep them cool. If you’re going to watch this movie then be sure to take notes on Steve McQueen’s character who dresses in one of the most iconic menswear outfits ever worn: men’s sunglasses and men’s hats.

The Great Gatsby (1974)

the best movies in men's style

Robert Redford wears a suit over a black polo neck; men wear waistcoats, men wear shirts with detachable collars and men wear vests under their suit jackets.
Fashion highlights include: men wearing slim-fit suits with wide lapels, men dancing in slim-fit tuxedos with peaked lapels, men in ’20s style flapper dresses.

Set against the backdrop of the 1920s jazz age in New York, this 1974 American romantic drama directed by Jack Clayton is another film adaption of F. Scott Fitzgerald’s 1925 novel of the same name.

The men’s fashion is inspired by 1920smen’s wear and men’s accessories, and it looks so good! Men wear slim-fit suits with wide lapels, men dance in slim-fit tuxedos with peaked lapels, and men wear waistcoats underneath their suit jackets. Men also like to dress up as men of the 1920s by wearing flapper dresses – or ’20s style flapper dresses at least (but sometimes men even go overboard). On the other hand, some men prefer to keep it simple with loose polo necks over a collared shirt, beige trench coats, white shirts and men’s sunglasses worn on top of hats.

The Talented Mr Ripley (1999)

men's style inspiration

Matt Damon wears a cardigan and slip-on shoes; menswear men’s sun hats, men wear men’s loafers. Fashion highlights include: men wearing men’s cardigans, men wearing men’s slip-on shoes.

Based on the first book of Patricia Highsmith’s five-part series, Tom Ripley is a talented young man who wants to become an integral part of the wealthy American society. The 1999 psychological thriller directed by Anthony Minghella is about how Tom Ripley goes from being a nobody to becoming somebody through conning and murdering his way to the top.

In this movie, men wear men’s sun hats, men’s loafers with socks; and Matt Damon even wears a men’s cardigan and slip-on shoes! Men can’t go wrong with traditional menswear basics – men’s trousers, shirts, and jackets.

The Soloist (2009)

style inspiration menswear

Robert Downey Jr. wears men’s wellington boots, and men wear men’s leather jackets. Fashion highlights include: men wearing men’s blazers, men wearing men’s gilet vests, men wearing men’s wellington boots.

Based on the true story of Nathaniel Ayers – a fictional character played by Robert Downey Jr. and Steve Lopez, who is a columnist for the LA Times – The Soloist tells the tale of two broken souls finding each other. In 2009 this modern-day remake directed by Joe Wright is another movie that features men in menswear basics: men wearing black suits, white shirts and men’s wristwatches.

However, viewers might notice more than men’s suits are men wearing men’s wellington boots (we can’t think of another movie character who wears men’s wellington boots). But men should know well enough to wear men’s leather jackets, jeans, and blazers when it comes to the final fight scene.

These were our favourites among best movies with style inspiration for men. Hope you find inspiration to dress stylishly with the help of these!

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