Y'know, I'd actually like it if characters in these shoenen animes had like three different outfits that they cycled through every season. It's kind of weird to think of Ash wearing the same set of clothes every day for an entire year or more.
Though yeah, maybe the hat is a legitimate gripe because he clearly cherished that original hat.
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"It's a magical world, Hobbes ol' buddy...let's go exploring!" - Calvin
http://img.imgcake.com/calvinfinalpngpy.png