The collection of images from the New South Wales Police Forensic Photography Archive on display at the Museum of Sydney are called The Specials, and they offer a rare insight into the city's criminal underworld in the aftermath of World War I.
One hundred and thirty photographs have been selected from an archive of more than 130,000 glass plate negatives and digitally scanned, revealing an extraordinary level of detail about society at the time.
Curator Nerida Campbell said there was still mystery surrounding some of the images.
"We don't know why they're called The Specials — that was the police terminology for them," she said.
"We're assuming it's because they sat outside of the normal.
"The roaring '20s was a time that many of us associate with glamourous socialites, cocktails, and dancing the Charleston. But this is the dark side."
Mugshots reveal changing times
The stories behind the characters are as fascinating as the photographs themselves.
Daisy Buchanan and Elsie Parker lured a travelling salesman into their home, stole his stock of bloomers, stockings and cash.
They then bundled him in a taxi and left him at a bus stop.
But they were found not guilty after the salesman proved an unreliable witness.
Samuel Guy was a flasher, but is seen wearing his very loose trousers very high up his waist.
In other photos, joy riders appear bruised and bandaged, and returned soldiers are seen struggling to fit back into society.
Mark Goggin, from Sydney Living Museums says the photos chosen are the "sweet spot" of the police archive.
"What you see here is how technology and societal changes, change the nature of crime," he said.
"You had motorcars becoming prevalent and so they start to get stolen.
"We've got alcohol becoming expensive so you get cheaper cocaine."
Photos prove influential
The unique portrait style was created by police photographer George Howard who snapped his subjects at Central Station's lock up — complete with hats, pearls and posing coyly like film stars.
They have also been the inspiration for fashion designers like Karl Largerfeld, and to the creators behind the BBC TV series Peaky Blinders.
"They're not like the traditional mugshots," Mr Goggin said.
"It's not the front and side, the people are standing some of them are laughing, they're holding cigarettes or they're holding handbags and conversations while their photos are being taken.
"So Sydney Police certainly took mugshots very differently to the rest of the world."
The exhibition opens at the Museum of Sydney on December 9.