When you think of a pirate, how do you envision him to be dressed? Do you picture him to be dressed in a peg leg and eyepatch with a parrot? Or to be more of a dandy like Jack Sparrow with a white linen shirt, dreads, and his ever-present hat?
Regardless of how you picture it, in reality, they dressed very practically. They wore the eyepatch to see below deck. They wore linen because it was cheap and breathable. A hat to block the shade. They dressed for the job they did and in a way that made sense. So when did we stop that?
Nowadays, we dress to look nice or to impress someone. But when did we go away from dressing in a way that is both practical and stylish? I do it myself, buying something that is deemed "cool", but not because it makes sense or is my kind of style. Why don't I just want to be comfortable, and is there a balance? Can you be dressed practically but also consistently be comfortable? I think there is a way to do both, but why is it that "high fashion" involves complex and intricate fabrics in ways that the average person cannot afford, let alone wear practically. Nowadays, you're not wearing an eyepatch to see below deck, you're wearing an eyepatch because "it's cool".
Everyone has their own personal style. But it has to make sense to who they are and what they do. So go on, and dress like a pirate.