Ok here goes.
On board the well rigged and armed pirate vessel: "The Jamaican Jive", The captain and first mate are Giles Lamont and Montague Lamont. They are non identical twins.
Giles
British
Black scraggly hair
Darker skin kinda middle to dark brown
Rugged black stubble on unshaven face
Not square jaw but definitely not feminine
standard height about 5'11
wiry build of a typical sailor
He has one eye that is really bad and one eye that is average giving him shaky depth perception (AKA Margaret Bray if harm remembers)
Wears no captain hat
standard gross worn billowly sailor pants but...
He has a very nice cuffed and collared black silk shirt with gold trim
He wears this shirt almost all the time. Only in the worst storms were his shirt may potentially rip he goes into his cabin and takes off his shirt going shirtless.
Family: Doesn't know he and his brother were british orphans
Bio: Well in a Jamaican port one day, a sailor got frisky with a local tavern wench. He left she gave birth to twins and decided she couldn't feed them both. Cast them out onto the street. (More info later Maybe)
Montague
Ermm... UP and coming.
By the way both their first names and their last name, they picked themselves listening to sailors talking amongst themselves in the port one day.