The Fantastic Fashion Worn By Sydney's Criminal Ladies in the 1920s

Daniel Holland
Sep 7
6 min read

Woman in 1920s attire stands by a wooden chair holding an object. Text reads "Fay Watson 24.3.28 D.6." Sepia-toned background. — Fay Watson, March 1928 – Fined £10 for cocaine possession

In the roaring 1920s, Sydney was a city of contradictions. By day, its sandstone buildings, trams, and docks hummed with commerce. By night, sly grog shops, gambling dens, and cocaine rackets thrived in the shadows. It was also the era of flappers, bobbed hair, and jazz — when women were claiming new freedoms.

Among Sydney’s underworld, women carved out a space of their own. Some were sly grog sellers, some cocaine traffickers, some thieves or madams. But what makes them unforgettable today is not just their notoriety, but their fashion. In a time when police photography was supposed to strip subjects of individuality, the mugshots preserved in the NSW Police Forensic Photography Archive reveal women draped in furs, pearls, and flapper frocks. They met the camera not as shamed criminals, but as stylish, defiant individuals.

Collage of vintage black-and-white portraits features individuals in various poses and attire, against plain backdrops with handwritten annotations.

The Camera’s Eye: George Howard and the “Special Photographs”

From 1912 to 1948, police photographers in Sydney, including the talented George Howard, developed a style of mugshot unlike anywhere else. Instead of the stiff, head-and-shoulders formula, they photographed suspects in full length, against plain walls or even casual backdrops.

Curator Peter Doyle, who co-authored City of Shadows, has noted that many of the sitters seem to be “performing” for the camera. They often chose their own stance: hands on hips, coats slung rakishly over shoulders, faces angled with pride or disdain.

As fellow curator Anna Cossu observed, these “Special Photographs” blur the line between documentary and portraiture. They show “human beings at a moment of great stress, and yet, they reveal humour, defiance, vanity, and style.”

In other words: these weren’t just mugshots. They were character studies.

Kate Leigh, 1915. she may have made her fortune selling illegal booze, but it was purely business. Ms. leigh never drank a drop.

Fashion as Defiance

The women of Sydney’s underworld knew the power of appearances.

Fur stoles and fox pelts gave an aura of wealth and resilience.
Cloche hats and feathered fascinators aligned them with the cutting edge of 1920s fashion.
Pearl necklaces and cocktail rings announced glamour in places where respectability was otherwise denied.
Tailored coats and drop-waist frocks made them indistinguishable from women of the middle classes.

Clothes were a shield, a performance, and often camouflage. Even in police custody, these women refused to be reduced to shame.

Three women pose for a photo against a wall. They wear 1920s dresses and hats, holding purses. Handwritten text with names and dates is above them.

Real Faces, Real Stories

Thanks to the City of Shadows exhibition and the work of Doyle and Cossu, we know the names and stories of many women captured in these extraordinary portraits.

Alice Cooke

At just 24, Alice Cooke had already lived under multiple aliases, married at least twice, and was convicted of theft and bigamy. Described by police as “rather good looking,” she posed in a smart suit, her expression calm and calculated. Cooke’s fashion sense, neat and businesslike, masked a chaotic personal life.

Alice Clarke

One of many women convicted of selling liquor without a licence, Clarke was a sly grog seller who thrived under Sydney’s restrictive drinking laws. Her attire was practical but polished, presenting herself as a respectable matron while profiting from the thirst of the city’s working class.

Annie Gunderson

In 1922, teenage Annie Gunderson was arrested for stealing a fur coat from Winn’s department store. Her mugshot shows her wrapped in fur — perhaps the very garment she was accused of taking. The photograph captures both the allure of fashion and the risks young women took to grasp a piece of it.

Dorothy Mort

The tragic figure of Dorothy Mort shocked Sydney in 1920 when she murdered her lover, Dr Claude Tozer, before attempting suicide. In her mugshot, Mort looks sorrowful and defeated, her understated clothing contrasting with the flamboyance of other women in the archive. Her photo reveals the devastating consequences of passion rather than the thrill of profit.

May “Botany” Smith

Famed for her violent temper, Botany May Smith was a cocaine dealer with dozens of arrests. In one infamous episode, she chased policewoman Lillian Armfield with a red-hot iron during a botched arrest. Her mugshot radiates defiance, smartly dressed, shoulders squared, a figure as dangerous as she was stylish.

Eugenia Falleni (Harry Crawford)

Convicted in 1920 of murdering his wife, Falleni lived for decades as a man under the name Harry Crawford. His mugshot is striking: dressed in a suit and tie, hair short and neat, his stern expression challenges the viewer to look beyond scandalised headlines. His clothing was not flamboyant but deeply authentic, a visual declaration of identity.

A person in a suit sits on a chair against a dark, textured backdrop. Text "234, E. Falleni" is visible above. The mood appears serious. — Eugenia Falleni - Known as Harry Crawford, Falleni was a transgender man who lived as a man for many years and was eventually convicted of the murder of his wife.

Tilly Devine

The great rival of Kate Leigh, Matilda “Tilly” Devine built a criminal empire of brothels and razor-wielding thugs. Her courtroom appearances were theatrical — tailored dresses, lavish coats, elaborate hats. Devine’s mugshots show a woman who wielded fashion as power, dressing not to hide but to dominate.

Dulcie Markham

Nicknamed the “Angel of Death,” Dulcie Markham was linked romantically to numerous gangsters, many of whom met violent ends. With platinum blonde hair and film-star looks, Markham was described as a “glamour girl of the demi-monde.” Her mugshots capture her beauty and her boldness, a young woman who understood how allure could be its own weapon.

Two women in fur coats, one seated with eyes closed and the other standing near a chair. Text "H. McGuinness, 26-7-29" on wall. Vintage setting. — Hazel McGuinness, July 1929 – Busted for cocaine possession along with her mother, Ada

Razor Queens and Rivalries

The most notorious figures, Kate Leigh and Tilly Devine, defined an era. Leigh, draped in fox furs and diamonds, ruled the cocaine trade and sly grog shops. Devine, every bit as fashionable, controlled prostitution and fought bloody turf wars with razors.

Their rivalry was the stuff of legend, played out both on Sydney’s streets and in its courtrooms. But their images endure not only as crime bosses but as style icons — the fur-clad queens of the underworld.

Young person in a checkered dress sits against a textured backdrop. Text "744.V.Lowe.15.2.22" is above. Somber expression, sepia tone. — Valerie Lowe, February 1922 – Breaking and entering, jewellery theft

Beyond the Glamour

It’s tempting to romanticise these women as flapper anti-heroines, but their lives were far from easy. Many came from poverty, endured violence, and lived precarious lives under constant threat of arrest.

Fashion, then, was survival. It helped them blend into respectable society, intimidate rivals, and resist a justice system that often punished women more harshly than men. As Doyle put it, the photographs show “not just criminals, but people trying to assert control over how they were seen.”

Sepia-toned image of a woman looking sideways, wearing a fur-lined coat and scarf. Text above her reads "20 Mrs Osbourne." Neutral background. — ‘Mrs. Osbourne’, around 1919 – Details unknown…except that she has fabulous velvets and a fantastic steely expression.

Legacy of the Archive

Today, the NSW Police Forensic Photography Archive is preserved by the Justice & Police Museum in Sydney. The City of Shadows exhibition brought these images to global recognition, showing them not as curiosities but as human documents.

Artists, designers, and historians continue to study them. The clothes and poses still inspire fashion shoots; the stories behind them remind us of resilience in the face of social marginalisation.

Black and white mugshot of a woman with curly hair, wearing a knitted top. "Vera Crichton, 21.2.24" text above. Serious expression. — Vera Crichton, February 1924 – Conspiring to procure a miscarriage

Conclusion

The women of Sydney’s criminal underworld in the 1920s lived dangerously, but they dressed magnificently. Their mugshots are not grim records but bold portraits, women draped in fur, pearl-strung, feather-crowned, staring down the lens with defiance.

In a city where crime, fashion, and modernity collided, these women left behind not just rap sheets, but a gallery of unforgettable images. They remind us that style is never trivial, it can be defiance, camouflage, and survival all at once.