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Appropriate clothing for Japan

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I've been googling in anticipation of my upcoming Japan trip and am quite surprised by some of the stuff I'm reading, which is along the lines of "NEVER wear jeans in Japan!" "NEVER wear sneakers" etc. and I just wanted to get a few opinions.

I normally dress quite smartly, but will be backpacking, so it's going to be hard to bring nice jackets and things - they will get all creased and wrinkled. Plus, I have a problem with my big toe joint on one foot, which means that my feet need a lot of support and wearing my beloved ballet flats or brogues for any length of time, like when walking around sightseeing, is out of the question.

I had been planning to bring quite casual clothes - blue jeans, leggings, oversized T-shirts, hoodies and cardigans, with maybe a couple of dresses in case I go anywhere formalish in the evenings. I was planning to wear my sneakers (Nike Air Max which are green/purple and almost new...they are cute and not my gym ones, but still sneakers) and maybe bring some light black ballet shoes to wear with anything dressy in the evening. Is this going to look really sloppy? I don't mind not fitting in with the Japanese, as I look obviously Western anyway, but I don't want to cause offence.

I was planning to buy clothes over there because I love the style (if anyone knows where to buy reasonably priced tees, blazers, sweaters etc in Tokyo, do recommend somewhere!), but shoes will be difficult due to my huge feet, and I need something to work with because I'll only be buying bits and pieces, not a whole new wardrobe!

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