As part of the Raven's Cove Story Quest, female pirates will have to disguise themselves as Sadie to get inside the Skeleton Poker club. The resale and purchase prices are the same for each individual article of clothing required, so you can sell the items right back and take back your investment.
Sadie's Clothes have to be purchased in order to get into the Undead Poker Club:
Seamstress Anne's Shop
Truehound's Tailor Shop
|Padres Del Fuego|
Dolores Tailoring Shoppe
Forest Knee Boots
If you stand up while doing the quest and you haven't gotten to 650, your gold will be reset and you will have to start over. If you are working on going for 5,000, you lose 500 gold every time you stand up. If you are caught cheating, you are sent to jail and lose 500 gold from the quest counter.