For shoes? The most I have ever paid I think was about 40 bucks. Usually I stick around the 20 or less range. Plus half of my shoes I've gotten were for free. Either from playing on a sports team where we got free gear. Example would be in college when I played for the baseball team, we got free gear. If we stay on the team the whole time we keep everything. If we get cut or decide to quit before the end of the year you have to return everything. So, in college I got 4 new shoes for free. One each year haha.
Now, when it comes to cleats, I've paid in the 120-150 range, but shoes... I try to keep it 20 and below but have gone up to 40 before.
What kind of shoes? It depends for what but for a dressy pair of shoes/business shoes I've paid $250+ but they're high-end Italian leather. The most expensive overall were my Adidas Adizero F50 Prime soccer boots in orange/black when they first released; I got them for like $350 and I've spent thousands in total on boots - it is my passion though so I don't dwell too much on the cost.
A lot. I don't have many pairs of shoes because they're so slim. They're so slim that even the slimmest fitting available in my country is too wide so if I want to wear shoes I have to be willing to order them from abroad or have them specially made more my feet. That's means I can't just wear whatever shoe I find in the shops like everyone else and if they're ugly but they fit, I just have to deal with that. Also they have to last me as long as possible :( Having Cinderella feet is not fun.
I don't buy really expensive things especially shoes. I don't buy my things lol, at 21 my mom still buy things for me because she loves shopping and I don't. The most I have paid was probably about 50 to 60 bucks sneakers.