Well, I bought the matching Tropical Mickey outfits for all of us in June before it was changed from Tropical night, so we just wore those. Many others did as well. I picked up the hats at a yard sale a couple years ago & they have been in the kid's dress up stash.
They have red bandanas on the tables at dinner & alot of people put those on their heads at both dinner & the party.
I think that the deck party started at 9:45 or 10 pm? I know that we went to see The Incredibles for the show that night and the movie ran long. I kept an eye on my watch to make sure that we weren't late for the party.
One thing that we did last cruise & again this cruise was bring the glow necklaces & braclets for the kids to wear at the party. They do sell them at the party but you can get a pack of 6 at the dollar store.
Next time I will be buying things for us to look more pirate like. I will wear black pants with a frilly blouse & maybe get a flouncy long skirt & blouse for DD. DH & DS can wear black pants & a loose white shirt with the pirate hats. IDK if we will wear them to dinner along with the party though. It was neat getting the kid's picture with Mr. Smee & Captain Hook before dinner with their pirate hats.

Captain Hook kept taking DS's hat. LOL! DS finally started saying "tick tock" and Hook tossed the hat at him.
There were several men dressed up & 5 of them were selected to go up on the stage to try out to be one of Hook's crew. They had alot of fun.