Jesus is talking to a group of people about what they as individuals should and should not do. All occurrences of "you" and "your" are singular. In some languages they may need to be translated as plural. (See: [[rc://en/ta/man/jit/figs-you]])
The "tunic" was worn close to the body, like a heavy shirt or a sweater. The "cloak," the more valuable of the two, was worn over the "tunic" for warmth and also used as a blanket for warmth at night.