In 1756, there were no prison uniforms in Europe. John Howard (1729-1790), an English gentleman appointed High Sheriff of Bedfordshire who very much took to his duties, first proposed a number of reforms to the British prison system in the 1770s - mostly to do with improving the conditions where prisoners lived - which included the provision of uniforms to replace the often tattered and filthy street dress the prisoners wore. Gloucester Reform Gaol, which opened in 1791, attempted to address all the issues of the old prison system and appears to have introduced uniforms - although there does not seem to be a clear record of what those uniforms looked like. Most sources believe that very late 18th century convict dress was composed of "parti-colored" pieces: clothing made with the right side one color, and the left another, the colors often switching sides on the lower half of the body. These might incorporate yellow, as in this uniform and this other uniform, both from Australia, or simply black and white or grey.

Clothing instead came in with prisoners, and new clothing would only be furnished if they could purchase it or had friends or family to send it. For instance, when the Marquis de Sade went into the Bastille in 1789, he had "a full complement of shirts, silk breeches, frock coats in camel-brown, dressing gowns, several pairs of boots and shoes; a selection of hats; three fragrances - rose water, orange water, and eau-de-cologne" (as quoted in Dress Behind Bars: Prison Clothing as Criminality, Juliet Ash); a poor man might have one shirt, a worn coat, threadbare wool breeches, and no stockings.

So, what's the situation of this convict? What was his life like before he went into prison? Is he just a random person for purposes of the illustration, or is this a character with a backstory? I can go into more detail about men's clothing if I know his life situation.