Leo was a scalawag who was at home in romancing Greenlee as he was at blackmailing others to get his way.
Hat: The scalawag's hat came in the form of a large bandanna that was placed over the head and tied in back.
There are many kinds of pirates, from the dapper and daring to the refined captain, and the scalawag we all know and love.
Footwear: A pair of oxfords or loafers will be well suited for the scalawag especially if they are discolored, scuffed and holy.
Traditionally the scalawag would be barefooted on deck and soles slip on wet would but that simply is not practical for you.