Smiler in a dress and wig in Gentlemen Prefer Blondes. Remember him handing out flyers in female garb as well in possibly another episode I cannot think of the name.
I think Auntie sold Compo an owl in a case but that could be a different episode, Dick.
I remember Smiler in a tuxedo falling through the roof of the Tom's delivery truck. Again episode name fails me. Will stop to let others have a chance.
Added.
Yes, Smiler was a good sport in wearing all the different outfits that he did. He was a likable character and am glad to see that he became part of the cast.