This article investigates the disguise of Duke Vincentio in Measure for Measure and that of Earl Kentin King Lear. It argues that through their disguises and downclassing, the two characters transgress theirelite social position to maintain further power, control, status, and authority. Their aims are geared towardsbenefiting themselves. M. C. Bradbrook relates disguises to a decrease in social status, and Patrick Churadefines downclassing as experiencing the harsh life conditions of the less fortunate classes. By consideringthese views and the two plays’ socio-political contexts, the article maintains that Shakespeare disguisedVincentio and Kent to suggest moral weaknesses on their parts. Also, Vincentio’s and Kent’s motives,social invisibility, and social roles determine and complicate their chosen forms of disguise anddownclassing. The article suggests that Kent’s disguise is more practical than the Duke’s. It concludes thatthe two disguises might indicate Shakespeare’s political mocking of the upper classes of his time.Keywords: Disguise, Downclassing, Social Invisibility, Measure for Measure, King Lear.