A good pair of boots are great. Something you can invest in, like Redwings, that will last and last and can even be resoled if needed to keep going.

But of course, having to remove shoes constantly in Japan makes wearing boots fairly impractical. Even many businesses require you to take your shoes off and don slippers. So I don't own any boots anymore. Sandals and flipflops look very dirty and sloppy to the Japanese eye, so they are not common for daily wear here.

At present I only own two pairs of shoes, in fact. Just my sneakers (currently an old pair of Nike Free) and my black dress shoes.