It sounds to me you are on the right track Second hand stores are the best place to find a tramp costume and as far as the hat goes whatever YOU think looks good with the rest of the costume
Skits Skits are short performences that have a set up (beginning) and a blow off (ending)that gets the laugh Try to find some old conedy tapes like Red Skelton to see some really clasic stuff
Hope this helps a little
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Laughter is music to Gods ears so laugh loud and long
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