In photos released by the Iraqi army after his capture, the man can be seen to have slathered on powder, eyeshadow and lipstick, even adding some beauty spots.
But the large moustache and beard as well as full eyebrows, rather give the game away.
Other photos released by the army show the men in padded bras as they try to slip through the net and out of the city.
Mosul’s Old City, which once stood as a neighborhood of densely built alleyways and homes on winding lanes, has been reduced to rubble by a months-long war to root out the Islamic State.
The effect of the battle, which ended as jihadists made their last attempt to hold on to the region earlier this month, can be seen in stark before-and after satellite photographs.
Much of the city has been leveled, with rubble and dust covering what was once a thriving neighborhood in Iraq.
Nearly a third of the Old City - more than 5,000 buildings - was damaged or destroyed in the final three weeks of bombardment up to July 8, according to a survey by UN Habitat using satellite imagery.
Across the city, 10,000 buildings were damaged over the course of the war, the large majority in western Mosul, the scene of the most intense artillery, airstrikes and fighting during the past five months. The survey only covers damage visible in satellite photos, meaning the real number is likely higher.