The Fantastic Fashion Worn By Sydney's Criminal Ladies in the 1920s
- Sep 7, 2025
- 9 min read
Updated: Aug 19
Sydney in the 1920s was a city living two lives at once. By day it was trams, sandstone banks and harbourside commerce. By night, sly grog shops, cocaine dealers and illegal casinos ran a whole second economy in the same streets. Women were at the centre of a lot of it, and when police finally caught up with them, an awful lot of these women turned up to their own mugshots dressed like they were heading to the races.
Furs, pearls, cloche hats and tailored coats show up again and again in the surviving photographs, and it wasn't an accident. For a lot of these women, looking sharp in front of a police camera was the last bit of control they had over how the world would see them.
Four Tonnes of Glass Plates: How the Archive Survived
None of these photographs were meant to last as art. They were forensic records, filed away and mostly forgotten once a case closed. For decades that's exactly what happened to them, boxed up in a NSW government warehouse in Lidcombe with no index and no case notes attached.
In the late 1980s the warehouse flooded, and what the Historic Houses Trust pulled out was roughly four tonnes of photographic material, a huge share of it still sealed in original Kodak boxes. It took writer and curator Peter Doyle roughly three years working alone in the loft of Sydney's Justice & Police Museum to work through the 130,000-odd images and figure out who was actually in them.
With no paperwork to go on, he cross-referenced faces against newspaper archives and police gazettes, piecing together names and stories decades after the fact. The result became the 2005 City of Shadows exhibition and book, the source for most of what's known about the women in these photographs today.
The Camera's Eye: George Howard and the Special Photographs
From 1912 to 1948, Sydney's police photographers, George Howard chief among them, shot suspects in a style nobody else in the world was really doing at the time. Instead of the stiff head-and-shoulders formula, they photographed people full length, often against plain walls or wherever happened to be handy, letting subjects choose their own stance.
Within that huge 130,000-image haul, around 2,500 negatives shot between 1910 and 1930 got a specific internal designation: Special Photographs, kept deliberately distinct from the standard prison mugshot record. Most were taken in the cells at Central Police Station, and curator Peter Doyle has written that their subjects were often, quite deliberately, invited to position and compose themselves however they liked. That single administrative decision, to let people plucked straight off the street pose rather than simply be recorded, is the whole reason this archive looks the way it does.
Curator Peter Doyle has pointed out that a lot of the sitters look like they're performing for the camera, hands on hips, coats slung over one shoulder, chins tilted with real defiance. Fellow curator Anna Cossu has described the "Special Photographs" as sitting somewhere between documentary record and portraiture, showing people under real stress who still found room for humour and vanity. They weren't just evidence. They were, whether the police intended it or not, character studies.
Fashion as Defiance
The women of Sydney's underworld understood exactly what clothes could do for them.
● Fur stoles and fox pelts signalled wealth and staying power, even for women one bad month away from ruin.
● Cloche hats and feathered fascinators put them on the cutting edge of fashion most respectable women could only read about.
● Pearl necklaces and cocktail rings announced a glamour that a criminal record was supposed to make impossible.
● Tailored coats and drop-waist frocks made them, at a glance, indistinguishable from the middle-class women the law was so eager to protect from them.
Clothes worked as shield, performance and camouflage all at once. Even standing against a police wall, these women weren't going to be reduced to shame.
The Woman Chasing Them
There's a useful bit of tension missing if you only look at the women in front of the camera. Standing on the other side of most of these arrests was Lillian Armfield, recruited in 1915 as one of the first two women in the NSW Police alongside Maude Rhodes, and later Australia's first female detective. Male colleagues disapproved of her for years. She worked cases solo and undercover anyway, chasing down exactly the kind of sly grog, cocaine and vice rackets Kate Leigh and Tilly Devine were building their fortunes on.
Armfield spent decades going up against the women in this archive, and by most accounts eventually earned a grudging respect from several of them, Kate Leigh included. It reframes the fashion a little. These weren't just women performing wealth for a faceless institution. A lot of the time, they were dressing to face down someone who actually knew who they were.
Kate Leigh and Tilly Devine: The Razor Queens
Two women defined this era more than anyone else, and they hated each other for most of it.
Kathleen Leigh, born Kathleen Beahan in Dubbo in 1881, had a genuinely brutal start: mistreated as a child, sent to Parramatta Industrial School at ten, released at fourteen straight onto the streets of Sydney. By her twenties she was running an empire out of her Riley Street house in Surry Hills, selling illegal alcohol after the pubs shut at six, fencing stolen goods, and eventually becoming the city's biggest cocaine supplier, a title that earned her the nickname the "Snow Queen." She was arrested a staggering 107 times over her career and served 13 separate gaol terms, and still somehow ended up remembered by plenty of Sydneysiders as a working-class hero who fed the unemployed during the Depression.
Matilda 'Tilly' Devine, born Matilda Twiss in Camberwell, started as a sex worker on London's streets before marrying an Australian soldier, Jim Devine, and following him back to Sydney in 1919. She racked up 79 convictions in five years before pivoting to running brothels around Darlinghurst and Palmer Street, using her husband Jim to move cocaine through them. A quirk in the law meant only men could be convicted of living off prostitution, which let Tilly stay technically outside a charge that would have sunk most of her rivals.
Both women got rich, both women dressed like it, and both went to war over territory. Razors, not guns, became the weapon of choice after NSW tightened firearms law in 1927, and the years that followed are still known as the Razor Gang Wars, running battles fought out in Darlinghurst and Kings Cross that left men dead, disfigured or doing serious time. The 1929 Vagrancy Amendment Act, aimed squarely at breaking up exactly this kind of operation, made it a specific offence to simply be seen associating with known criminals or prostitutes. It didn't stop either woman for long. The feud didn't formally end until 1936, when police commissioner William Mackay leaned on both of them to accept a truce.
Kate Leigh died in 1964, aged 82, at St Vincent's Hospital. Tilly Devine's later years were far less kind: a 1955 tax bill for $20,000 forced her to sell off most of her properties, and by 1959 her once-sprawling brothel network was down to a single address on Palmer Street.
Still Being Told
Leigh and Devine's feud was still compelling enough to build a television series around eight decades later. Underbelly: Razor, the fourth season of Australia's long-running true crime drama anthology, ran for thirteen episodes on the Nine Network in 2011, with Danielle Cormack and Chelsie Preston Crayford playing Leigh and Devine and Lillian Armfield written in as a recurring character on the other side of the law. It's a reminder that this isn't a forgotten footnote of Australian history. It's a story people are still choosing to tell, dramatise and watch.
Real Faces, Real Stories
Thanks to Doyle and Cossu's research, plenty of the women in the archive have names and stories attached, not just charge sheets.
Alice Cooke, just 24 when she was photographed, had already lived under multiple aliases and married at least twice before her convictions for theft and bigamy. Police called her rather good looking, and she posed in a smart, businesslike suit that gave nothing away about the chaos underneath.
Alice Clarke sold liquor without a licence, one of many women who thrived under Sydney's restrictive drinking laws. Her attire in the photograph is practical and polished, a respectable matron's look built to disguise exactly what she was profiting from.
Annie Gunderson was just a teenager in 1922 when she was arrested for stealing a fur coat from Winn's department store. Her mugshot shows her wrapped in fur, quite possibly the very coat she was accused of taking, a single image that captures both the pull of fashion and the risk young women took just to get near it.
Dorothy Mort's photograph sits apart from the others entirely. She shocked Sydney in 1920 by murdering her lover, Dr Claude Tozer, before attempting suicide herself. Where most of the women in this archive dressed to project confidence, Mort's mugshot shows someone sorrowful and defeated, her plain clothing a world away from the fur-clad defiance elsewhere in the collection.
May 'Botany' Smith was one of Leigh's rivals in the cocaine trade and was known for a genuinely violent temper. In one infamous 1928 arrest, she went after Lillian Armfield herself with a red-hot iron. Her mugshot radiates exactly that defiance: shoulders squared, smartly dressed, a woman as dangerous as she was stylish.
Eugenia Falleni, convicted in 1920 of murdering his wife while living for decades as a man under the name Harry Crawford, sits in the archive dressed in a suit and tie, hair cut short and neat. Falleni's full, complicated story is covered in depth elsewhere on this site, but the mugshot alone says something the others don't: clothing here wasn't performance or camouflage, it was simply the truth of who Falleni was.
Nellie Cameron grew up in a comfortable North Shore family and attended a respectable girls' school before running away at sixteen straight into the Darlinghurst brothels. Newspapers called her the "Kiss of Death Girl," a nod to how many of her lovers, including Frank Green and Guido Calletti, ended up shot, stabbed or dead entirely because of the men who wanted her. She holds a genuinely unusual legal footnote too: the first woman in Australia ever convicted under the new 1929 consorting laws that were supposed to break up exactly this world. She took her own life in 1953, aged 41, having quite literally outlived every gangster who'd fought over her.
Dulcie Markham, nicknamed the "Angel of Death", might be the most extreme story in the whole archive. A sex worker by 15 and a gangster's girlfriend by 18, she went on to lose at least five lovers and two husbands to shootings and stabbings across three decades, earning newspaper headlines calling her the woman who'd seen more violence than anyone else in Australia's history. Remarkably, her story doesn't end in tragedy. In 1972 she married a sailor, Martin Rooney, settled into a quiet two-storey house in Bondi, and by all accounts became, in her husband's own words, a wonderful housewife who wanted to forget the past. She died in 1976 in a house fire after falling asleep smoking in bed, and was buried not as Dulcie Markham, gangster's moll, but simply as Mrs Rooney.
A Gallery That Refused to Look Ashamed
The women of Sydney's criminal underworld in the 1920s lived dangerously, but an unusual number of them dressed magnificently while they did it. Their mugshots aren't grim records so much as bold portraits, women draped in fur, strung with pearls, staring down a camera that was never supposed to let them look like this.
In a city where crime, fashion and modernity kept colliding, these women left behind more than rap sheets. They left a gallery of images that still argue, a century on, that style can be defiance, camouflage and survival all at the same time.
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For the full story behind one of the archive's most striking figures, read The Life and Crimes of Eugenia Falleni: A Complex Legacy.
For another city where women ran the underworld their own way, see Girl Gangs of Old New York: Marm Mandelbaum and the Underworld Women of the Gilded Age.
Sources
9. Revisiting the City of Shadows: Police Photographs Record Petty Crims, Accidents and Crime Scenes
