Thanks guys for your responses.
Yeah, I'm going to Tokyo solely to meet my girlfriend, but wouldn't mind marketing the brand we have here in the US there in Japan.
And they might be flat billed when you buy them, but you get both hands on them and curve them a little bit. HAHAHA, just joking.
Yeah, I also thought that it'd be a pain in the a$$ to take about 100 hats, so I was just thinking of taking the best samples I have currently, (although we create 15 new designs every week), and show them and tell the stores that we will ship to them with express or priority mail.
Thanks guys once again for your help. I'll keep the customs issue in mind, but with me, I can just say it's all my gear... which it is.