When in doubt... check the wiki!
http://www.disneyonlineworlds.com/index.php/PIRATE_LIFE
^^ must be level 10
http://www.disneyonlineworlds.com/in...T_FOR_A_PIRATE
^^ must be level 15
http://www.disneyonlineworlds.com/in...RIA%27S_FAMILY
^^ must be level 20
The only other clothing quests are specials (as in, you cant get them anymore).
-Captain