/fa/ - Fashion

I own one pair of shoes. Pic related. I just buy them on Amazon, wear them til they wear out, then buy them again. I wear them to work, out and about, and when dressing up. I wore them to graduation this summer, and it probably looked awful, but I didn't care. I think I should start caring.
I have foot problems (bear weight on my metatarsal heads), so I need a shoe that can accommodate a Powerstep insole insert, making most dressy shoes incompatible. I also can't wear anything with a heel due to the pressure it puts on the ball of the foot.
I need more shoes. Where do you guys buy shoes? Buying online is risky, I hate not trying before I buy, that's part of why I just keep buying the same thing, I know it fits.