On Sunday August 23rd 1851 a hard fought riot broke out in Sydney. Whilst such disturbances were common place at the time this particular riot is interesting in that it was sparked by the arrest of a sailor for wearing women’s clothing, was led by military men and involved attacks on a number of police watch-houses. Despite police and newspaper reports of the incidents being confused and often contradictory the riot tells us much about attitudes of Sydney’s population towards cross dressing, police and the law.