Fashion loves a bad boy and they don't come much rougher than Sidney Kelly, a well-dressed career criminal who cut a swathe through Sydney's demimonde in the 1920s.

The last time Kelly sat for a formal portrait a representative of the NSW constabulary was holding the camera - his picture is one of more than 130,000 collected in the forensic photography archives of the Justice & Police Museum.

Now Kelly is turning heads again, this time in New York and London, as the unlikely muse for designer Ralph Lauren's latest menswear campaign.

The billionaire American has purchased the rights to a series of police mugshots of Kelly and other Sydney thugs, conmen and criminals to adorn his flagship stores in New York and London and help inspire a new advertising campaign.