Top 10 Best Dressed Mobsters of All Time

Life in the mob has its ups and downs, from constantly looking over your shoulder, making risky deals, and trying to work your way to the top, right through to the large amounts of money in your pockets, luxury cars, big houses, and dining at upper-class steakhouses every night of the week.

If you got the money, then if you are anything like the mobsters in our top 10 list, you’re gonna flaunt it. And one way of flaunting it is buying expensive suits and always looking the part. Whether you’re on a contracted hit, or sipping an Espresso at a cafe, suited and booted is the way to go.

Mobsters back in the 20th century certainly knew how to dress – they had style, class, charisma. With that said, let’s get on with our top ten best dressed mobsters of all time starting at number 10.

– Joe Adonis #10

Joe Adonis was an instrumental part in the early days of the National Crime Syndicate, and helped the likes of Luciano and Lansky take control of the Mafia, by removing Joe The Boss and Sal Maranzano, and forming the modern day Cosa Nostra.

Adonis wasn’t his real name — his real name was Giuseppe Antonio Doto. Speculation has it that he adopted the name himself, a reference to the Greek god of beauty. He spent a great deal of time on his personal appearance, with daily grooming routines. On one occasion, Luciano caught Joe Adonis combing his hair in front of a mirror and asked him:

“Who do you think you are, Rudolph Valentino?”

Adonis replied:

“For looks, that guy’s a bum!”

You would always see Adonis wearing a fedora and the finest suits New York had to offer. He was always well presented, with not a hair out of place.

– Paul Castellano #9

John Gotti summed up Big Paul in one sentence: Paul was just a businessman who never served his time on the street and got his hands dirty. That businesslike approach extended to his appearance — Castellano spent a great deal of time on the materialistic things in life, and one of those was how he looked.

As a mob boss, he could afford anything in life, and he was spotted in a suit in pretty much every photograph ever taken of him. As a man who preferred to run his criminal empire like a corporation from the White House on Staten Island rather than from the streets, looking the part of a successful executive was essential. He even died looking the part, stepping out of his car outside Sparks Steakhouse in a well-pressed suit before John Gotti’s hit team opened fire.

– Jim Colosimo #8

Big Jim Colosimo may have been assassinated as early as 1920 — making him by some distance the oldest entry on this list — but he still made an indelible impact in the Moustache Pete era of the Mafia. He was the original boss of what we now call the Chicago Outfit, as well as being known for his restaurant at 2126-2128 South Wabash, Chicago — one of the most popular dining establishments in the city before Prohibition arrived.

As you can see from the photograph, he was always a well-dressed character, sporting a flat cap, suit and leather gloves, and sometimes pictured with a cane. For a man of his era, when most Italian immigrants in America were dirt poor, the quality of his clothing was a statement of power as much as personal vanity.

– Lepke Buchalter #7

The Murder Inc crime boss who ended up on the Sing Sing electric chair in 1944, brought down by informant Abe Reles. Lepke — whose actual name was Louis — would often be seen suited and booted, complete with the stereotypical mob hat. He would also complete his look with a handkerchief in his suit pocket and a matching overcoat.

Whether he was being escorted by his cronies into a courtroom, smiling at the camera or giving a ruthless look, he was always dressed to impress. For the man who ran the most prolific murder operation in American criminal history, he maintained a remarkably civilised exterior.

– Al Capone #6

One of the most notorious mobsters of the early 20th century, made famous for his violent temper and scar down his face — giving him the nickname “Scarface,” which he personally hated, preferring to be called Snorky. Most photographs show Al Capone with a cigar in his mouth and a felt Panama hat.

Capone also wore a gold pocket watch complete with chain, which was clearly visible against the tone of his charcoal suits. Despite having scars down his face, personal appearance meant a great deal to Capone and he would ask photographers to always shoot the right side of his face rather than the scarred left side. His style was deliberately ostentatious — a statement of wealth and power in an era when most Italian immigrants in America were poor. Read about Al Capone’s net worth →

– Bugsy Siegel #5

If Bugsy Siegel wasn’t a mobster, he would have fitted right into the 1940s Hollywood acting scene. He was a charismatic character who charmed the ladies and had film star good looks — frequently compared to actors of his era and genuinely welcomed into their social circles. Underneath was a darker side: he was one of the mob’s more violent members, with a hair-trigger temper that had earned him the nickname Bugsy, a period slang term for someone erratic or crazy. He hated it.

Wherever Bugsy was, he was always dressed to wow the crowds. Whether wearing his famous polka-dot suit completed with handkerchief and pinky ring, sporting a pin-striped suit, or donning a Panama hat, he always looked like he meant business. He even died looking dapper, shot in Virginia Hill’s living room while elegantly dressed. Read about Bugsy Siegel’s net worth →

– Meyer Lansky #4

The mob’s accountant, Meyer Lansky was the financial genius behind the Mafia in its most important era. He wasn’t just Lucky Luciano’s sidekick — he was the mastermind behind the casinos in the US and Cuba, the architect of the money laundering systems that kept the mob’s profits invisible, and one of the most important organised crime figures of the 20th century.

Being such a prominent character, it goes without saying that Lansky was always well dressed. Preferring the cigarette to the cigar, he would be seen in charcoal suits, sometimes with his Panama hat. For a man who was the most important financial operator in American criminal history, he dressed with the quiet elegance of a successful Wall Street banker — which, in many ways, is exactly what he was. Read about Meyer Lansky’s net worth →

– Frank Costello #3

The Prime Minister of the Underworld, Frank Costello, had politicians, judges, policemen and mayors in his hand. He was influential in decisions that changed history and changed the way the Mafia evolved in the US — from a major gambling empire to controlling elections, he was one of the most powerful mob bosses who ever lived.

Costello craved the respectability of high society, so he agreed to testify at the Kefauver hearings rather than take the 5th amendment. Dressed in a grey suit with a handkerchief in his left jacket pocket, Costello cut a noble, distinguished figure — exactly the image he cultivated. His hat was also made famous when Vincent Gigante’s assassination attempt in 1957 ripped through it but only grazed his head. Read about Frank Costello’s net worth →

– Charles Luciano #2

Lucky Luciano was the founding father of organized crime after he successfully planned the assassination of Joe The Boss and Sal Maranzano back in the 1930s. It was after these hits that a new era of the Mafia began, with a Commission and a structure to the families. Luciano turned crime into a fully fledged business model and if he wasn’t in a life of crime he would have made a great CEO of a major company.

As the boss of bosses, Luciano had to be taken seriously, and he dressed to look the part. Heads would turn as he walked down the street, with some thinking he was an A-list Hollywood celebrity rather than a crime boss. Lucky would sport the finest pin-stripe suits in his heyday, completed with a Panama hat. He always made sure he looked dapper, and even in his ageing days in exile in Naples he still dressed with elegance. Read about Lucky Luciano’s net worth →

– John Gotti #1

John Gotti is one of the most talked about mobsters of the late 20th century — a crime boss who enjoyed the limelight and managed to duck out of criminal charges three times, earning his nickname the Teflon Don, before finally being convicted in 1992 on the testimony of Sammy “The Bull” Gravano.

He broke many old-time rituals and Mafia rules and some say the Mafia fell apart because of him. Whether you like or hate John Gotti he was an extraordinary dresser, and has been stereotyped as your typical Mafia don — bringing the Godfather to life on the streets of New York.

It’s his second nickname that earns him this top spot: the Dapper Don. Gotti wore hand-tailored Brioni suits that cost thousands of dollars each. He would finish any look with clean pressed suits, a handkerchief in the pocket, a pinky ring, hair neatly swept back and sometimes an expensive cashmere scarf. His annual clothing budget was estimated by FBI investigators at between $30,000 and $100,000 — expenditure that was itself used as evidence of unexplained wealth.

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