But prison officials said the nervousness displayed by Clauvino da Silva, also known as "Shorty", as he tried to leave the prison in the western part of Rio de Janeiro dressed as a woman gave him away.
His plan was apparently to leave his 19-year-old daughter inside the jail.
Police are looking into her possible role as an accomplice in Saturday's failed escape attempt from Gericino prison.
Rio's State Secretary of Prison Administration released photos showing da Silva in a silicon girl's mask and long dark-haired wig, wearing tight jeans and a pink shirt with a cartoon image of doughnuts.
They also released a video in which da Silva can be seen removing the mask and some of the clothes, and saying his full name.
Authorities say da Silva was part of the leadership of the Red Command, one of the most powerful criminal groups in Brazil that controlled drug trafficking in a large part of Rio.
After the failed escape bid, da Silva was transferred to a unit of a maximum-security prison and will face disciplinary sanctions, officials said.