Why do they repeat them?
 

Q. Why do they always repeat the outfits every year?

A. The outfits are repeated each year so that pirates who never got them before have a chance to purchase them.

Lets take an example here:

Name: Joe Pirate
Started playing: 2007
Outfits purchased: all

Name: Pirate Joe
Started Playing: 2013
Outfits Purchased: Barbary Corasair and Snap Dragon