So, You Want to Dress Like a Gangster? A Guide to Men’s Mafia Style

Fashion inspiration can be found everywhere, but for a lot of like-minded men, there’s often a common source for our sartorial awakenings. We’re talking about movies, particularly mob flicks. You know, the classics. The Godfather. Goodfellas. Scarface. Casino. And many, many more.

Think of the first time you saw Michael Corleone (Al Pacino) in his sharp, pinstripe suit, ready to step into the role of don. Or when we as an audience first see the all grown-up Henry Hill (Ray Liotta) sporting a sharkskin suit and popped black collared shirt in Goodfellas (1990). Chances are, if you’re anything like us, you thought to yourself, damn, that guy looks cool as hell.

Morals of the movie aside (a life of crime rarely pans out well), the glitz and glamor is present in both the clothing and stylistic choices of cinema’s most famous mobsters. We can’t advise that you mimic their lifestyle, but we totally get wanting to steal their look.

Interestingly enough, a lot of (though not all) the fashion seen during on-screen portrayals of both real and fictional gangsters is very much based on real-life historical trends. So, if you’re looking to dress like a wiseguy, we’ve got just the guide for you, breaking down various looks you can replicate yourself!

Gangster Look: Wearing the Right Suits Part 1 – The Don

One of the first garments people are quick to associate with wiseguys is the suit. However, taking into account various eras and decades of tailoring, not just any suit will do. It takes some finesse!

A lot of the tailoring you might see in films like The Godfather (1972) or during the young Vito Corleone (Robert De Niro) flashback scenes from The Godfather 2 (1974) is highly reminiscent of the clothing from their respective time periods in which they take place.

Though he begins the film in military garb and ivy style, Michael Corleone’s suits become darker and more conservative once he embraces his new role in the family. His gray, charcoal, and black pinstripe suits are both dramatically roomy and finely tailored, with three-piece suits and double-breasted jackets featuring peak lapels making many appearances.

These outfits are seen as the pinnacle of mafia style, and denote a degree of status and importance. You can mirror this style by paying attention to the fit and features of your suits.

For “The Don” look, seek out full-cut Italian tailoring with a focus on gray and charcoal, or even a deep navy blue, with pinstripes, chalk-stripes, or subtle windowpane patterns. Go for wide, fuller lapels on the jacket (a given if it’s double-breasted) and a higher rise on the pants.

Silk suspenders (with the attachment buttons sewn into the pant waist) are another core detail, as are the occasional cuffed leg, single or double pleats, and sharp shoulder lines along the jacket.

Be sure to pair your “don” suit with dark dress shoes, like dark brown or black oxfords. Opt for dress shirts in a crisp white or striped pattern, as well as a fuller, pointier collar. Medium-to-wide ties are a must, and should be proportionate to the width of the lapels.

Gangster Look: Wearing the Right Suits Part 2 – The Regular Wiseguy

The “golden days” of organized crime, especially for the American mafia (AKA Cosa Nostra) took place largely during the 1950s and 1960s. And though the RICO act of 1970 eventually brought on its downfall, the style of wiseguys in the 1960s, 70s, and 80s has stuck with the American consciousness due to the enduring popularity of films like Goodfellas, Mean Streets, Casino, Donnie Brasco, and others.

Like much of the country, a lot of mobster style got, well, rather groovy in the 70s, and deeply influenced the perception of gangsters in the latter half of the 20th century.

Sleeker, sleazier suits, pointier collars, and bold colors dominated the culture, and gangster style often followed suit (pun intended).

Perhaps no film better encapsulates these stylistic features than Martin Scorsese’s mob epic, Goodfellas. From Henry Hill’s iconic vertical-striped knit polo worn open over a ribbed tank top (complete with wide-leg trousers and loafers), to the more severe character looks served throughout the film, there’s a lot to draw from here.

On the more casual side, 70s tailoring works tremendously well for a gangster look. Think double breasted suits with sharp, padded shoulders and subtle flared legs, paired with big floppy disco-esque collars popped over the jacket’s lapels. Oh, and of course, a nice pair of loafers.

You can also opt for a sharkskin suit, provided the proportions are retro and accurate, paired with a more casual shirt (popped collar optional).

Sharp as a Switchblade

If you’re trying to get a slightly dressier look while still drawing from the 70s mobster style, spearpoint collared dress shirts are certainly the way to go.

While the incredibly long, narrow collars worn by Joe Pesci, Ray Liotta, Robert De Niro, and company were tailored exclusively for the production of Goodfellas, slightly less dramatic versions of these shirts can be found on the secondhand vintage market.

But if you want the exact look of the titular “fellas” and their deadly-sharp spearpoints, we recommend checking out this made-in-Italy Spearpoint Cotton Shirt by British brand Thomas Farthing – it perfectly replicates the style.

For the rest of a sharp, contemporary gangster look, follow similar suiting trends as outlined in “The Don” section mentioned earlier. Darker colors, with full-fitting jackets and trousers, and pinstripe, herringbone, or birdseye patterns and textures.

Gangster Look: Side Pieces

If there’s one thing about a stereotypical mob guy – it’s that they take advantage of an opportunity to accessorize.

Gold watches (especially thinner styles), gold and silver chains, bracelets, and more are all fair game and fall in line with the overall aesthetic.

But perhaps it is your selection of rings that could end up counting the most. Old-school mobsters often sported various rings, often adorned with precious stones and crafted from high-end metals.

Pinky rings are somewhat considered the most ostentatious of the bunch, though you can get pretty wacky with the other digits as well.

Our take? Experiment, but with caution. Wear what feels right and wear jewelry you’re personally drawn to. It’s a lot easier to pull off the more natural it feels. That means it could take some prep until you’ve worked your way up to a pinky ring, but that’s part of the fun, isn’t it?

Gangster Look: Cool and Casual

Mob style isn’t all about suits. Just take a look at Tony Soprano, perhaps television’s most famous waste management consultant from HBO’s critically acclaimed series, The Sopranos. Tony wears his fair share of fine Italian tailoring to be sure, but he’s a modern guy in the early 21st century. He’s suburban.

Tony Soprano’s casual style makes for a great blueprint that encapsulates wiseguy attire that doesn’t demand the inclusion of a suit. Even outside of the context of mafia style, there’s a lot to draw from Tony’s wardrobe for everyday looks.

To get the look, try wearing full-fitting, double-pleated tailored pants in shades of tan, gray, and black, and pair them with expressive bowling shirts, camp collar shirts (worn over a tank, naturally), and knit polos. Invest in quality leather shoes such as a good pair of loafers or derbies, and make sure to sport a nice watch. Other flashy accessories (as mentioned above) are welcome too, of course.

Mafia Style: Wiseguy Wisdom

The best mafia style is often reinforced by the right surroundings, and while you can certainly embrace and incorporate these ideas into your everyday personal style, it helps to rock it in the right light.

That is to say, experiment with it slowly and appropriately. It can quickly look and feel as if you’re simply wearing a costume if the context is all wrong. Try to imagine doing a Sunday grocery errand in a three-piece pinstripe suit. A bit odd, isn’t it?

But out to a nice romantic dinner? At a posh supper and jazz club? That’s what we’re talking about. Half the reason a lot of these looks appear so effortlessly cool is because the on-screen mobsters are doing cool things.

So, that’s our final recommendation. Skip the life of crime (seriously). But embrace doing the types of cool things that make the style feel more natural. There’s no time to waste. Get your sharpest Italian double-breasted suit, pointiest spearpoint collar shirt, a silk tie, some loafers, and get over to the Copacabana, ASAP.