One of the places i NEVER go for clothing is Cuba, they have about 2 pages of green clothes that vary SLIGHTLY in tone lol. I always go to Tortuga for the corsets, Port Royal for the pants and boots, and sometimes Padres when i feel like dressing royal lol. They should offer more holiday related clothing, maybe halloween we can dress as ninjas... (now that would confuse those that begin playing on Halloween - "hey this is a pirate game i joined what's going on!")
Also, the Tortuga corsets for the ladies you can't get anywhere else, not as a beginning item either
But a way to get some rare clothes on new pirates you create, pick a clothing item and choose a color you can't buy in the stores.