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How To Dress Like A Mobster

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Mobsters are our favorite kind of bad guys. They are the bad guys we love to hate! Whether it’s Goodfellas or The Sopranos, Bugsy Malone or The Godfather, we can’t get enough of their tough-stuff antics.

And that is why we absolutely love to dress as mobsters for costume parties and Halloween. It is great fun getting to take on a big-shot persona for one evening, and mobsters just so happen to have pretty iconic style too!

So, if you are thinking of throwing together a mobster outfit for your next fancy dress party, then you have come to the right place.

We have the top tips on how you can achieve that instantly recognizable gangster look, and we cover gangster girlfriends too!

Man posing in the dark with a fedora hat and a trench coat

Head Gear

Let’s start at the top and work our way down, because really, there is nothing that screams mobster more clearly than your classic trilby hat.

A trilby hat is a very specific type of fedora hat that has been around since the early 1900s. It was originally designed by Scottish milliner James Craig in 1902.

He called his creation “the Trilby” after the character from Jules Verne’s novel Around the World in Eighty Days.

woman wearing black trilby hat

Trilbys were initially worn by men who wanted to emulate the dapper gentlemen of the era. But they didn’t stay this way for long. The trilby gained notoriety when gangsters started wearing them. 

Some even went as far as to claim that it was invented specifically for them. That might be true, especially because of the way that the narrow brim can be worn very low over the brow in order to cast a shadow over the wearer’s face and obscure their identity.

Michael Jackson made the trilby particularly iconic when he wore a black and white one in his gangster themed music video for the smash hit Smooth Criminal.

Michael Jackson Smooth Criminal Record Album

If you wear nothing else to a costume party but a trilby, people will probably still recognize that you have come as a mobster!

Wide Neck Tie

Working our way down the body, the next item that any mobster outfit should include is a long, wide necktie.

Ideally, this tie would be black or white and would contrast directly with the color of the shirt you are wearing. The effect is a stand-out emblem of pretend “conformity”; something that real mobsters took very seriously. 

You see, even though mobsters of the 1920s were criminals, they had to give off the appearance of legitimate businessmen in order to carry out their dealings.

The oversized tie is a great way of capturing the facade of decency and respectability that mobsters hid behind.

Mysterious Mobster in red neck tie -

Pinstriped Suit

In the 1920s, pinstripes were all the rage. Mobsters had many different reasons for wearing pinstripe jackets and trousers, but the most obvious was that it was stylish.

As mentioned above, gangsters wanted to appear respectable and well mannered, which meant that they needed to dress up in clothes that looked good. Pinstripes gave these outfits an extra edge.

They also helped make the wearer seem taller, making him appear more imposing. This was very important for when mobsters needed to intimidate others in order to get their way.

A great tip for any gangster costume is to choose a slightly oversized suit jacket.

Large shoulder pads and long sleeves are a comical way of depicting the lack of moral stature that these mobsters had beneath their showy clothing.

young man in pinstripe suit standing against a brick wall


If you don’t know what spats are then you’re not alone. They are basically little boots that go on your shoes. They are usually made of leather and have laces that run all the way through them.

Spats actually came into use during the 19th century. They were originally used on horses to keep dirt off the rider’s feet.

Eventually, they became popular among gangsters because they allowed them to walk without getting their expensive trousers mucky.

The problem with spats is that they don’t look good on anyone other than gangsters. So if you want to go all out and really capture the essence of the 1920s mobster, then you need to invest in some proper shiny Italian leather footwear too!

You wouldn’t want to end up looking like a clown!

Traditional white spats worn over black boots

Far Cigar

Another thing that mobsters loved doing was smoking cigars. In fact, they smoked so much that they often ended up being overweight.

This was a big part of why gangsters were stereotypically depicted as being fat. It was considered to be a sign of wealth and power.

So if you want to really capture the spirit of the 1920s mobsters, then you need to add a cigar to your costume.

Tommy Gun

Now, we arrive at a truly quintessential piece of equipment that every mobster should own. A Tommy gun.

Gangsters were known for carrying guns everywhere they went. It was their trademark accessory.

But what exactly does a Tommy Gun look like? Well, it’s basically a submachine gun.

What makes it unique is its size; it’s about 3 times bigger than the average handgun. 

The Mobster’s Carpet Bag

The final piece of equipment that every mobster needs is a carpet bag. These bags were usually black or dark brown and were designed to hold everything that mobsters carried around.

In addition to being practical, they also served another purpose – they could be used to hide weapons.

This was especially useful for gangsters who were carrying guns. It was not uncommon for mobsters to carry concealed weapons while going about their business.

So there you have it. All the essential items that you need to complete your perfect mobster costume.

Gangster Girlfriend

red haired flapper girl gangster girlfriend in black dress and white pearls

Finally, let’s take a look at the girlfriend. She needs to be dressed like a gangster’s moll.

A great way to capture the essence of the era is to dress as a flapper girl, complete with 1920s headband, flapper dress, and long cigar holder.

Gangsters often owned and ran illegal drinking clubs during the time when alcohol was prohibited in America. For this reason, many of their wives and girlfriends worked as dancers in these clubs.

Finishing your gangster moll outfit with a faux fur coat, finger wave, and beauty spot will really seal the deal!

Final Thoughts

Dressing as a mobster and a mobster’s Moll couldn’t be easier. There is no need for complicated makeup or home crafting.

All you need to do is stick to a mainly black and white color scheme and make sure that you get those iconic items in the bag!

Oh, and don’t forget – you’ll need to adopt a fabulous Mobster accent to complete the effect. “Make him an offer he can’t refuse”!