Mug shot and criminal record of Eugenia Falleni, from Sydney, Australia.
Falleni lived as a man named Harry Leon Crawford and married Annie Birkett in 1914. Allegedly Falleni killed Birkett when the secret was discovered three years later. (It is not known whether Falleni was in male clothes when she was arrested, or if the police made her dress that way for the shot.) Falleni plead not guilty but was convicted and sentenced to death in 1931. The sentence was commuted and Falleni lived under yet another assumed name for seven years before dying of injuries after being hit by a car.
The worst part of this story, if you can pick just one part, is that apparently Falleni was under the (incorrect) impression that it was illegal in Australia to dress as a different gender, which probably goes a long way to explain everything that happened subsequently. Her life could have been—should have been—much different.
(Source: collection.hht.net.au)