Anna Sorokin -

Anna Sorokin, also known as Anna Delvey, is the famous con artist who tricked New York's elite into believing she was a German heiress. She managed to work her way into the most affluent circles of society and had almost secured millions in investment for her business plans before she was revealed as a fraud. Sorokin used her impeccable taste and confidence to get as far as she did, and even her court appearances were covered by fashion magazines. Her incredible story was dramatized in the Netflix series 'Inventing Anna.'

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The most stylish criminals in history -

When it comes to pulling off a major crime, it's usually important not to draw suspicion. How does one do this? By blending in with the crowd, of course! Considering that the object of most criminal plans is money, then blending in with a rather elite crowd is essential. And there's no doubt that looking good and moving with confidence opens doors (sometimes to con artists, scammers, and thieves).

Intrigued? From Anna Sorokin to Butch Cassidy, click through this gallery to see some of the most stylish criminals in history.

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Anna Sorokin -

Sorokin was sentenced to four to 12 years in prison for grand larceny in 2019, but was released for deportation back to Germany in October 2022. She was seen stepping out in a stunning all-black outfit shortly after her release, perfectly accessorized with her ankle monitor!

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Mata Hari -

Mata Hari was a Dutch exotic dancer at the beginning of the 20th century, famous for her seductive beauty and unique style of dance learned during her time living in the East Indies, now known as Indonesia and Malaysia. She fabricated a fantastical backstory for herself, claiming to be born in an ancient Indian temple where she learned the art of dance, and dressed the part to amaze European audiences.  She had romances with high-ranking military officers and politicians from many different countries, making her a valuable asset when World War I came around.

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Mata Hari -

It was believed that she acted as a spy for the French who recruited her to seduce the German Crown Prince Wilhelm to obtain information. However, they later accused her of acting as a double agent for the Germans, and she was executed for espionage by the French in 1917.

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Bugsy Siegel -

Bugsy Siegel is the mobster credited with building Las Vegas up to the gambling and leisure mecca that it is today. He liked to live big and luxuriously, so much so that he started funneling money from the casino projects he managed for his investors. These business partners were not people who took kindly to being cheated, and Siegel was gunned down in 1947.

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Virginia Hill -

His girlfriend, Virginia Hill, helped him to siphon the funds and deposit them in European bank accounts. However, she wasn't simply the mistress of a gangster. Hill herself was known as the "Queen of the Mob" and ran operations for the Chicago Outfit gang for more than a decade. Her good looks and charm are said to have helped her ingratiate the Chicago mob with the Mexican cartel to set up a drug trafficking scheme.

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Elizabeth Holmes -

Elizabeth Holmes was a ground-breaking young entrepreneur in biotechnology who turned out to be a fraud. Through her dogged commitment and belief in her company, Theranos, she secured millions in investment and was seen as the wunderkind of the tech industry. She rubbed shoulders with A-list celebrities and met the likes of Joe Biden and Bill Clinton.

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Elizabeth Holmes -

Holmes styled herself after Steve Jobs, wearing almost the same outfit each day–a turtleneck sweater under a pantsuit, all in black, with red lipstick. When she hit the red carpet, which she did on a number of occasions, she stuck to her signature color and always looked sleek and sophisticated. Unfortunately, her invention wasn't as well thought out as her wardrobe, and she was convicted of fraud in 2022.

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Bonnie and Clyde -

While the real Bonnie and Clyde might not have been quite as stylish or beautiful as Faye Dunaway and Warren Beatty in the 1967 film that told their story, they still had the swagger to become the most notorious criminal couples in history.

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Bonnie and Clyde -

The bank-robbing duo looked like a perfectly nice, well-put-together couple, with Bonnie in her pencil skirts, knit sweaters, and beret, and Clyde in his dapper suits. Their stylish exteriors hid their reckless lifestyle, as they lived on the run from the FBI and carried on a crime spree that lasted almost two years. They were eventually gunned down by police and killed in 1934.

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The Bling Ring -

The Bling Ring, also known as the Hollywood Hills Burglar Bunch, were a group of seven youngsters from the Calabasas area outside of LA. They notoriously targeted the homes of the rich and famous, stealing their cash, clothes, and jewelry while they were out of town. The group reportedly burgled around 50 homes, including those of high-profile celebrities like Paris Hilton and Orlando Bloom. Alexis Neiers (left) and her sister Tess Taylor (right) were two of the teenagers involved.

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Patty Hearst -

Patty Hearst was the stylish young heiress to a publishing fortune when she was kidnapped by a group of leftist extremists called the Symbionese Liberation Army in 1974. She was allegedly coerced into joining their cause, extorting millions from her father and committing bank robberies with the aim of feeding all the hungry people in Los Angeles.

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Patty Hearst -

Hearst spent more than a year with her captors and appeared to have developed some kind of Stockholm syndrome, adopting their views and their Che Guevara-inspired attire. Once captured by the FBI, she was charged with the bank robberies, but eventually had her sentence commuted.

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The Wild Bunch -

The Wild Bunch were the most successful train-robbing gang in the history of the Wild West. The criminal group included famous outlaws like Butch Cassidy and the Sundance Kid. You can tell they turned a nice profit just by looking at their outfits!

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Jeremy Meeks -

Jeremy Meeks' story is beyond belief. The handsome felon was a member of the Crips, the notoriously violent Californian street gang. Meeks was arrested in 2014 by the Stockton Police Department, who put his mugshot on their Facebook page, as they had done for every arrest since 2012. However, Meeks' mugshot went viral with hashtags like #feloncrushfriday.

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Jeremy Meeks -

Meeks was convicted of grand theft and illegally carrying a firearm in 2015. After serving 13 months, he was released and began a successful modeling career based on his viral fame.

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John Dillinger -

John Dillinger was a famous gangster active during the Great Depression in the 1930s, leading the Dillinger Gang in robbing countless banks and even some police stations. In every photo captured of him, he looks confident and at ease, as if he doesn't carry an ounce of guilt for all the crimes he committed.

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John Dillinger -

Dillinger's dangerous swagger may be what gave his look that extra edge. He was best known for wearing simple white shirts with a black waistcoat, perhaps with a loosened tie, and always had his hair slicked back. He was played by Johnny Depp in the 2009 film 'Public Enemies.'

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Evelyn "Billie" Frechette -

Billie Frechette was a singer who dated Dillinger for about six months. She is quoted as having said, "John was good to me. He looked after me and bought me all kinds of jewelry and cars and pets, and we went places and saw things, and he gave me everything a girl wants. He treated me like a lady." She once drove a getaway car for Dillinger after he was shot and let him hide from the police in her apartment. She was arrested for obstruction of justice in 1934.

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Charles Ponzi -

The name Ponzi is famous these days thanks to one Charles Ponzi, and the money-making scam he invented in the 1920s. The slick con artist started an investment racket where he convinced his marks to invest in a non-existent enterprise by promising a huge return on their investment once more investors had been secured. This model is now known as a Ponzi scheme and has been used countless times in the past century.

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Pearl Hart -

Pearl Heart was a famous female outlaw who has gone down in history for her criminal escapades. She is notorious for having carried out the last-recorded stagecoach robbery in 1899.

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Pearl Hart -

Hart carried out the robbery dressed in men's clothing. She reportedly took pity on the passengers after taking all of their money and gave them back one dollar each so they could buy some food. She was caught and imprisoned, but it's believed that she charmed several men into helping her escape.

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The Kray twins -

The Kray twins, Ronnie and Reggie, were two of London's most notorious gangsters. The identical twins dominated organized crime in the city for two decades with their gang, which was known as the Firm. They epitomized the Italian mobster look of the 1960s, but with that extra London flair. They were both sentenced to life imprisonment for their countless crimes in 1969.

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Comtesse de La Motte -

The Comtesse de La Motte, whose real name was Jeanne de Valois-Saint-Remy, was a con woman active just before the French Revolution (which some say she may have started!). She passed herself off as a stylish noblewoman and a friend of Queen Marie Antoinette. She befriended a wealthy cardinal and convinced him to buy an extremely valuable diamond necklace as a gift for the Queen.

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Comtesse de La Motte -

She managed to make off with the jewelry herself by forging letters and enlisting a Marie Antoinette lookalike. It came to be known as the Affair of the Diamond Necklace, and spawned the false rumor that Marie Antoinette was buying diamond necklaces for herself while the country was at the brink of financial collapse and her people were starving. The French Revolution followed shortly after.

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Jesse James -

Jesse James (left) was one of the most famous outlaws of the Wild West. He's been photographed in three-piece suits as well as his more casual bandit attire, many elements of which have come back into fashion with a vengeance. Following a successful 20-year career of robbing banks and trains, he was shot and killed in 1882 at the age of 34.

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Lucky Luciano -

The Italian-born gangster known as Lucky Luciano is considered the father of organized crime in the US. He was always immaculately dressed in fine Italian suits, creating the archetype for the slick mobster.

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Wolfgang and Helene Beltracchi -

Wolfgang Beltracchi and his wife Helene pulled off some of the most stylish crimes in history. The seemingly artsy bohemian couple were actually responsible for some of the most scandalous art forgeries in history. Wolfgang is a talented artist who forged hundreds of works by the likes of renowned artists such as Max Ernst and Heinrich Campendonk.

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Wolfgang and Helene Beltracchi -

Helene acted as the art dealer and helped to sell his forgeries to wealthy collectors. They were caught and convicted in 2011, by which time it's estimated that they had earned more than US$100 million. 

Sources: (Complex) (Mental Floss) (AskMen) (Esquire)

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