Long-time Genovese soldier David Petillo did it in drag.
Petillo was born in NYC in 1908, and during "his early teens was reputed to be a 'fairy'" and later developed a fetish for dressing in drag including when he killed a victim or two according to FBI documents.
It's very likely that Petillo was initiated into the criminal underworld as a male prostitute. The term "fairy" in Petillo's teen years was the English translation for finocchio which was a euphemism for the male prostitutes -- often underage -- who worked at brothels in Little Italy. For example, in Gay New York: Gender, Urban Culture, and the Making of the Gay Male World 1890-1940 (1994), historian George Chauncey writes:
The contrast between Italians and Jews, the two newest and largest groups of immigrants in New York at the turn of the century, is particularly striking. A 1921 study of men arrested for homosexual "disorderly conduct," for instance, reported that "the Italians lead" in the number of arrests; at a time when the numbers of Italians and Jews in New York were roughly equal, almost twice as many Italians were arrested on homosexual charges. More significant is that turn-of-the-century investigators found a more institutionalized fairy subculture in Italian neighborhoods than in Jewish ones. The Italian neighborhood of the Lower East Side had numerous saloons where fairies gathered interspersed among the saloons where female prostitutes worked. In 1908, Vito Lorenzo's saloon, located at 207 Canal Street (near Baxter), was charged by the police with being a "fairy place." In 1901, agents conducting a systematic survey of "vice conditions" on the Lower East Side found male prostitutes working at two Italian saloons on the block of Elizabeth Street between Hester and Grand, the same block where the Hotel Zaza's manager hired rooms to female prostitutes who stood at the windows in "loose dresses and call[ed] the men upstairs." One investigator noted that the Union Hall saloon was crowded with old Italian men and several young fairies on the night of March 5; a few doors up the street, at 97 Elizabeth, stood a saloon where the fairies, aged fourteen to sixteen, could "do their business right in [the] backroom." A month later the same saloon was said to have "5 boys known as [finocchio, or fairies] about 17 to 25 years of age." * * * The patterns of homosexual behavior noted in Sicily appear to have persisted in modified form in the Italian enclaves on the Lower East Side, in Greenwich Village, and in East Harlem. * * * [I]t seems likely that an important part of the homosexual culture of fairies and their sex partners visible in turn-of-the-century New York represented the flowering in this country of a transplanted Mediterranean sexual culture.
The vice rackets in which Petillo later was engaged certainly would be consistent with his roots as a fairy or finocchio. In 1936 the cross-dressing gangster was arrested on white slavery charges "with 100 prostitutes and madams and was described as an individual who had organized 200 houses of prostitution under LUCIANO with 3,000 girls grossing $12 million a year." The girls were happy to testify against Petillo, and he served 20 years at Sing Sing until paroled in 1956.
Upon his release from Sing Sing Petillo trafficked heroin for Vito Genovese through his gay bars, and in the mid- and late-1960s allegedly had a hidden interest in an afterhours club at 11 East 16th Street. Petillo further became involved in the pornography racket, and during the late 1960s and early 1970s was suspected of having an interest in Arrow Laboratories which produced some of the more hardcore material available at the time. Throughout the 1970s Petillo was "active in operation of sex-related businesses in New York City" and cocaine trafficking.
On February 4, 1980 Petillo murdered Edward Vassallo a/k/a/ Charles Talbot, and fled the country. He died in Spain on December 28, 1983, and no word on whether Petillo was buried in a dress.