Top 10 Stylish Gangster Movies: Ranking Hollywood’s Hoods

Hollywood loves gangsters for their glitz, flash, devilish charm, and admittedly, sometimes stylish yet over-the-top looks, which help underline their character. Today, we talk about the ten most stylish gangster movies and their noteworthy menswear ensembles.

The gangster genre rose to prominence in the 1920s when the whole Prohibition era definitely had an impact on it along with Vitaphone, which allowed for sound in movies. The sound of tommy guns made for infamous and larger-than-life storylines, and, along with the anti-Italian sentiment, movies like Little Caesar, The Doorway to Hell, or Scarface became popular.

Hollywood stars like Edward G. Robinson or Humphrey Bogart became popular through gangster movies. Of course, that’s also true for James Cagney or George Raft. The genre has stood the test of time and has led to masterpieces from Martin Scorsese, Francis Ford Coppola, or Brian de Palma.

Big-time gangsters, both in movies and in real life, were particular about their appearance. Al Capone, Bugsy Siegel, and Lucky Luciano were all known for the way they dressed. While their actions were not the least bit gentlemanly, they understood the power of their appearance and what it could make them look like in their community.

Top 10 Stylish Gangster Movies

We limited ourselves to one film per director to create our list, and we didn’t look at the acting at all. This is purely an appreciation of menswear.

10. Bonnie and Clyde (1967)

Starring Warren Beatty, Faye Dunaway, and Gene Hackman, this movie got two Oscars. Its graphic violence paired with a less structured plot shocked moviegoers at the time. It basically depicted the 1930s era of the rural Midwest and their take on the Golden Age of menswear.

It showcases how men going through this huge economic crisis, and even when doing blue-collar dirty work, still paid a lot of attention to their appearance.

In the film, you see a few slick suits worn by Beatty and Hackman, but also more casual workwear that was still classic, worn by Hackman and Pollard. Of course, we can debate how popular leather jackets and jeans were at the time.

We placed it lower on the list because to get some details wrong, such as wearing a belt with a three-piece suit and a vest, and unstylish looks like odd suit separate combinations. Though, admittedly, it was probably done on purpose to highlight the difficulties people were going through at the time when they couldn’t afford a proper suit and just had to make do with what they had.

As a true menswear aficionado, you will notice the 1960s influences on what is supposed to be 1930s clothing. And I know the 30s had shorter and wider lapels compared to the 60s, where they were a little narrower. To learn more about suits and the different changes throughout the decades, we created a guide on the Evolution of Menswear, which you may find really interesting.

9. Scarface (1932)

We chose to go to the 1932 version and not with the ’83 version because that, admittedly, had some Miami Vice gangster vibes, and they’re just not as classic anymore as the true original movie. Starring Paul Muni in front of the camera, you had Howard Hawks and Howard Hughes behind the camera.

The storyline of the film was loosely inspired by Al Capone and the film really shocked the Hays Codes board and had to be cut and censored numerous times before it was finally released to the public. 

Everything about this movie is excessive, not just the violence, but also the plaids, the stripes, and even the diamond weave pattern suits that you can see in this movie.

Of course, you also had fedoras tilted slightly sideways, you had ties, stick pins, bold stripes, and shirts paired with patterned suit jackets. An example would be a checked suit with a fine checked shirt, a nonchalantly put-in pocket square. Of course, you’d also see a tommy gun, and in one scene, people in Black Tie with pocket square, boutonnieres, and hats shooting up a bowling alley.

Overall, you probably want to tone down their style. But, it is a great example of having patterns of different scales combined. Want to match patterns in menswear to always look the part? We recommend checking out our guide.

One of the reasons we have it lower on the list is the fact that it’s a black and white movie, so it’s hard to imagine what it would actually look like in color. For the same reason, we omitted movies like Little Caesar or Angels with Dirty Faces.

8. American Gangster (2007)

Denzel Washington plays Frank Lucas and his rise to organized crime in New York. A key component of Lucas’s character is a very traditional, old-world business sense and drive for respectability. It’s taught to him by Harlem mobster boss Ellsworth “Bumpy” Johnson.

This also translates into his clothes. He always wears cufflinks, has bold dress shirts, sometimes with a taupe suit or a double-breasted suit. His lapels are typically peaked and have this kind of tautz lapel look, where the gorge line points straight out to the sides.

While most of the other male characters don’t live up to Frank’s style standards in the movie, it’s worth looking at the ethos of how important it is to portray yourself in a certain way. You can take it in real life, just leave all the stuff from the movie behind.

The irony of the theme is that when Lucas breaks that code himself by wearing chinchilla fur, it is the start of his decline. I can pick up many interesting details such as the slanted pockets, including the ticket pocket on a double-breasted suit or the aforementioned tautz lapels.

There are also real issues. For example, look at a tie knot and how it’s way too big for this kind of shirt collar spread. That’s definitely not a hallmark of a well-dressed gentleman.

7. Road to Perdition (2007)

Starring Tom Hanks, it’s about a Depression-era mob enforcer, who got framed by the son of a mob boss and now has to clear his name. It also stars Daniel Craig and Paul Newman, and it’s, in fact, one of his last on-screen performances.

The film showcases a number of different styles within the golden era. It goes from Hank’s “everyman” style to Stanley Tucci’s dandified suits. Paul Newman’s donning somber three-piece suits, and Jude Law also has a very unique style, including bowler hats.

The characters’ personalities are expertly showcased through their wardrobe. Pay close attention to Newman and Tucci in this movie because they are the clotheshorses, and they coordinate their pocket watches with their patterned suits and the colors.

Upon close inspection, though, you can see details don’t add up. For example, the bowler hat of Jude Law is actually a modern one, not a vintage one. How do we know that? It’s actually the brim curl. 

6. Casino (1995)

We could’ve put Scorsese’s Goodfellas in this spot as well, but we decided on Casino because it features a lot of different outfits, it’s bolder, and it fits the scene of that town.

Starring Robert De Niro, Joe Pesci, and Sharon Stone. It loosely follows the story of the mob’s racket with the Stardust Casino in the 1970s.

De Niro’s character Ace Rothstein steals the show here with over 40 different outfits; the true eccentric Vegas suits, his sport coats in pastel colors, and pinks. But, you can also find orange and yellow, and even if he wears blue, it’s a bold look.

For example, he wore a color-coordinated pocket square, shirt, and tie. Definitely not something we recommend you’d wear. Nevertheless, some of the color coordinations are interesting and bolder, and I think you can utilize that in your outfits. 

For example, yellow dress shirts are quite underrated. Though, I’d argue, if you go that route, don’t wear a matching pocket square in the same color. That’s definitely a 1970s approach that is not a hallmark of a well-dressed gentleman.

Pesci is also a good example of how you can use clothes to make yourself look taller when you’re a man of modest height. It definitely brings to life the unique culture around Las Vegas. Just make sure you avoid the whole “stuck up in the desert on the way there.”

5. Get Carter (1971)

A British production, it really is the polar opposite to Casino because the outfits are much more muted and modest. Michael Caine plays the gangster Jack Carter, who is out for revenge because his brother was killed in cold blood.

Despite a gritty subject matter, Carter’s style is as somber as it gets. You see him wear quintessentially British three-piece suits with a dark tie and a dark trench coat. There are not as many costume changes, but the fit is spot-on, and the lapel is neither too narrow nor too wide.

You could wear this outfit pretty much today without looking like you’re from the 70s, except maybe for the watch or the cufflinks, which definitely have a distinct 70s flavor. For a timeless look go with something like the monkey fist knot cufflinks from Fort Belvedere. They will stand the test of time and never look like they’re out of style.

4. The Godfather Part II (1974)

Curious about part one? Check out our in-depth analysis!

With six Oscar wins, it was the most successful sequel to date and it shows the decline of Michael Corleone and the rise of young Vito Corleone. Clothes-wise, the interesting part is that it spans several decades of menswear, the characters you should probably pay close attention to are Vito, Michael, and Tom Hagen.

Of course, there are also other characters like Don Fanucci wearing the white three-piece suit with a matching hat, socks, and slippers. His tie has a stick pin, the shirt is white, he has a little pinky ring, and a gold tooth, and on his left lapel, you see this like black strip, which is a nod to his nickname of the “Black Hand”.

Let’s also look at Michael’s suits, which vary in shades of grey. I particularly like his three-piece suit, which is very somber and classic. Also, I really like Vito’s brown striped suit, which is distinctly more vintage.

Note the much shorter lapels, which are quite wide and have that nice round-cut belly. When you look at the vest, it’s a rather high cut, so you only see a very tiny bit of the tie knot, but not much tie exposed otherwise. That was something you wore at the time to just protect your shirts more and to keep warmer, not a style you’d see today anymore.

Hagen, on the other hand, has a style of his own. He’s the attorney, but he wears things like a seersucker suit with a dark tie, for example.

There are some historical and fit inaccuracies just like in the first part. Nevertheless, there’s a lot to admire in this movie, and I hope you just don’t tell Michael about it.

3. Once Upon a Time in America (1984)

Much like The Godfather Part II, the story plot of Once Upon a Time in America spans several decades, so you see a bunch of different outfits, and the character and their development is also highlighted through the clothes they wear.

The film follows David “Noodles” Aaronson from the early bootlegger era, all the way into his late age in the 1960s.

De Niro and Pesci are once again characters you should pay attention to. It even features nice Black Tie outfits with detachable wing collars, self-tied bow ties, and vests worn with tuxedo jackets. Also, you can pay attention to the pocket styles, the belted backs, as well as the tie patterns. With a run time of four hours, you should definitely walk away with some style inspiration.

2. The Untouchables (1987)

Of course, you can’t have a list of stylish gangster movies without Al Capone and The Untouchables did a good job in our opinion. The movie follows Elliot Ness played by Kevin Costner trying to take down Al Capone, who is played by, yes, you guessed it, Robert De Niro. Sean Connery also won an Oscar for his role as Jim Malone.

Not only does the movie do a good job in recreating Capone’s outfits, such as his famous trial suit. But, it also highlights a number of other different styles from characters other than Capone himself.

Elliot Ness has very traditional white-collar business suits for example. On the other hand, Sean Connery has a bit more rustic clothing, which is really nice to see as a contrasting point, which, again, underlines their characters. Or you can see a bit of casual flair with brown suede jackets as worn by Andy Garcia. If you want to see the Golden Age of menswear on full display, in color, this is your movie.

Of course, just make sure you never bring a baseball bat to a Black Tie event.

1. The Sting (1973)

While some might argue it’s a bit of a stretch to put this movie in the gangster genre, we put it here because it’s loosely in there and the clothes are just splendid. Starring Robert Redford, Paul Newman, and Robert Shaw, this movie won seven Oscars including the one for Best Costume Design, which went to Edith Head.

The film takes a lighter tone in the 1930s and displays styles from all social classes. There’s great detail in costuming and you can find everything from tie stick pins, spats, spectators, tab collars, detachable collars, and so forth. It’s worth noting that while filmed in 1973, it was set in 1936. And here and there, you can see the 70s influence in this film.

For example, the shirts and the tie prints are definitely bolder than what they probably would have been in the 1930s. They’re more in line with the 70s. At the same time, you don’t see gapping collars or other small errors in terms of fit that you usually see in Hollywood productions.

In fact, a lot of the outfits were directly pulled from old-fashioned illustrations from the 30s. Just look at the gray peak lapel, windowpane suit from Paul Newman paired with a darker motif printed tie, and a gently striped shirt next to the brown striped suit of Robert Redford paired with this bold 70s tie. I also like their great Black Tie ensembles.

Note the cummerbunds and the shawl collar on Paul Newman’s jacket and the nice 30s peaked lapel, which is more of a tautz lapel, pointing out on Robert Redford. They both have cufflinks, they have shirt studs, and a nicely tied bow tie with detachable collars.

As a regular, you already know that, but if you’re new here, we have the world’s most comprehensive guide on Black Tie on our website and it’s free. Go check it out.

Apart from Newman and Redford, also pay attention to the clothes of Harold Gould. Everything he wears is stunning, including the pearl tie stick pin and the real tall club collars. Make sure you save your money for the clothes you want to buy afterwards and don’t put it all on red.

Outfit Rundown

I, of course, had to wear a 1930s gangster outfit. I’m starting with this really nice navy blue fur felt hat
from Miza and I had a vintage ribbon put on, so it works really well with my suit. It is a 30’s-inspired suit from Ralph Lauren Purple Label that was made in England. It is really soft, has these nice, wide lapels, and the nice 6.2 double-breasted cut.

It was, in fact, the first quality suit that I bought as a teenager on eBay years ago. Now, my white dress shirt with French cuffs has a classy collar, and I’m wearing it with a silver collar clip that has ball ends, and it works well with my silver or white gold cufflinks. I chose lapiz and silver from Fort Belvedere to pick up on the blue tones in the outfit. I’m pairing it with a white gold pinky ring and a blue star sapphire, which, again, picks up the tones of blue.

Of course, I needed a white linen pocket square in a square fold and I combined it with a vintage tie that has tones of blue and kind of magenta pink. My boutonniere is a Christmas rose in a pinkish-red that picks up the color of the tie.
It is handmade from 100% cotton velvet and really stunning inverse. You can find it in our shop along with numerous other handmade boutonnieres.

The shoes are a pair of gray suede and navy spectators with more of a 30s style from J.FitzPatrick. The socks are navy and blue two-tone solid socks from Fort Belvedere and you can find them in our shop.

What changes would you make to our list, and why? Let us know in the comments below!