This question came in a while ago but I haven't got around to answering it until now.
In Kansai, I like shopping in Namba, Shinsaibashi centergai and America Mura in Shinsaibashi and Sannomiya in Kobe. There is one Kansai shop called 'cook jeans' whose clothes I really love but I just hate their craftsmanship. Every piece of clothing I get from them has had a problem with the stitching so threads unthread and buttons fall off really quickly. They describe their clothes as 'Tough, wild and cool'. I think it suits me well.
In Kanto, I like Shibuya. I was in 109 mens the other day and I got some boots. A lot of their stuff is geared towards host kei and gyaru-o so I'm not really into a lot of it anymore, getting a little more mature with my clothing style, but there were a few shops that I would drop more cash in. Harajuku used to be cool a few years ago, but not anymore for the same reasons.
Other shops I like; Zara is pretty cool at times. Uniqlo is cheap and has simple T's that are nothing too fancy but be sure to walk down the street and see someone else wearing the same thing. JEANSMATE! Open 24 hours MOFO! Get it at 3pm or 3am- good for simple tops. Try to check out the underground shopping in all major shopping areas too. There are often clearance places that have a variety of goods at good prices. I also prefer to get shoes from clothing shops rather than shoe shops, however it depends on the item; I got some boots from ABC mart a month or two ago. Usually I hate ABC mart. For suits and work stuff I like 'comme ca store' or 'perfect suits factory'. If I'm stretched for cash I go to 'Aoyama'. A lot of young guys might think spending money on something you will wear to work is a waste, I say; 'never underestimate the appeal of a man in a well fitting suit knocking off work and loosening his tie over a cold drink.'
In other words, you don't only work in work clothes.
As for sightseeing; I like all sightseeing. I'll go anywhere and everywhere, but nothing stands out above what any other travel guide could detail more clearly.
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