OP, let your 5 year old son wear that pirate costume where ever he wants, let him enjoy every minute of it, take a ton of pictures, have an awesome time and don't give it another thought.
There will be boys and girls all over WDW dressed as pirates and don't think for one minute your little boy will feel out of place. If anything the characters will probably make a bigger fuss over him.
My son, who is going on 12, wore a pirate costume one night when we ate at CRT, he was 6 at the time and LOVED being a pirate. I look back at those pictures now with such love for that little boy that is now so big. Childhood is fleeting, embrace it every chance you get!!!!!![/QUOTE]
I totally agree! My son is 15 and I still think back on his last
MNSSHP party when he was Jack Sparrow (he was 11) - he cracked me up walking around like Jack, talking like him.. Just too funny and a memory I will always have. Enjoy every moment!
Don't forget they offer packages at the Pirate League now. So don't be surprised if you see more pirates wandering around. They aren't full costumes, but still a lot of fun.