Aww, that's a cute picture. And he's got the pirate wink down.
I dress Gigi up each Halloween. Last year I colored her hair with a mix of red food coloring and water, which dyed it pink. I then made a little thin cone hat so that she could be cotton candy. I did take her out trick or treating, but forget about her keeping her hat on. I still got a lot of compliments on her pink hair, though. Here's a few pictures I took with her cone hat on:
And here she is with with her fancy schmancy collar:
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