- Oliver Ridgeway
- Olivia Drench
- Olivier
- On the Horizon
- Oni Face Tattoo
- Onyx Double Band
- Onyx Double Lip Ring
- Onyx Ear Double Loop
- Onyx Ear Rings and Stud
- Onyx Full Nose Jewelry
- Onyx Hoop and Rings
- Onyx Knuckles
- Onyx Large Ear Loop
- Onyx Lip Spike
- Onyx Lip Spike and Rings
- Onyx Ring Spike
- Open Cotton Shirt
- Open Fire
- Open Fleet Shirt
- Open Laced Shirt
- Open Linen Shirt
- Open Long Sleeve Shirt
- Open Short Sleeve Shirt
- Open Treasure Long Sleeve
- Open Treasure Shirt
- Open Vest
- Open Vest (male)
- Opera Blouse
- Operation: Shipwreck
- Options (Menu)
- Orange Cream Candy Cane Sabre
- Orange Tricorne
- Orange and Green Tribal Arm Tattoo
- Orange and Green Tribal Full Sleeve
- Orangutan Blunderbuss
- Orangutan Broadsword
- Orangutan Cutlass
- Orangutan Doll
- Orangutan Repeater
- Orchard Vest
- Orgullo
- Oriental Doll
- Original Molten Cavern
- Original Padres Del Fuego
- Original Pillager's Pass
- Original Port Royal
- Original Tortuga
- Orinda's Shack
- Orinda Le Jeune
- Ornate Broadsword
- Ornate Cutlass
- Ornate Doll
- Ornate Key Arm Tattoo
- Ornate Pistol
- Ornate Repeater
- Ornate Sabre
- Ostrich Hat
- Outcast Isle
- Ovenmaster
- Overseer Staff
- Owen Collier
- POTCO Release Notes - 2007
- POTCO Release Notes - 2008
- POTCO Release Notes - 2009
- POTCO Release Notes - 2010
- POTCO Release Notes - 2011
- POTCO Release Notes - 2012
- POTCO Release Notes - 2013
- POTCO Savvy Swashbucklers
- POTCO Soundtrack: Outcast Isle
- Padded Cannon Ram
- Padres Del Fuego
- Pain-in-the-Bee-hind
- Pain Link
- Pal's Guide to HAVING FUN!
- Palifico
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