No I'm talking a "caricature" of a cowboy. I mean wearing an outfit like this:
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Or getting cosplayed up like this based on some cowboy from a cartoon:
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Wearing a cowboy hat and boots isn't the problem. COSPLAYING as one is. Remember he was cosplaying as a video game character in Shibuya. Nobody does this. The Japanese people would have seen him as a freak.
If Chibi went to Shibuya in a school outfit that looked like a normal school outfit, didn't look crazy and wasn't trying to cosplay as some character it would have still been retarded but not as retarded. It's the idea of going there specifically to cosplay as Joker that was the issue. It would be like him showing up in Japan wearing a kimono and insisting that he has to wear it everywhere. There's nothing wrong with wearing a kimono. It's just those tend to be reserved for special occasions.