Crossbones (Modern)
When Ed Brubaker took over writing the monthly Captain America comic, he added a real world, espionage tone to the book. Characters sstarted looking less like super-heroes and more realistic. Take Crossbones for example.
The right-hand man to the Red Skull, Crossbones went from wearing a sleeveless shirt to a combat vest and military boots. His look went from "wussy pirate" to a "kick-ass commando". And Crossbones tops it off with his trademark Mexiacn wrestler style skull mask which says, "I'm gonna kick you in the huevos". It's a bold fashion choice, and Crossbones pulls it off like a champ.