When commissioning a portrait, a pirate may choose to hold a portrait item. Specific items are available only if the pirate meets the criteria necessary for those items. (Some items exist that can be held only by Ringers at this time.) In any event, regardless of how many items the pirate has available to choose from, he may use only one such item at a time (i.e. only one item per portrait). Note: It is not possible to hold an item in the free portrait available from the "Get yer portrait painted!" mission.