For a while I was buying $80 Kenneth Coles and replacing them twice a year. I stopped doing that. Here's what I learned:
1. You need multiple pairs. Leather needs to dry. Don't wear the same pair of shoes two days in a row.
2. Some brands are worth the money. $400 for a pair of designer label shoes may not ensure quality, but paying in the $250-300 range for Allen Edmonds and such is completely worth it.
3. Shoes of the quality mentioned in #2 are seriously comfortable once the leather is broken in. They will save your feet.
4. Conservative, classic styles are the way to go for your first few pairs.
Right now, my rotation is 2 pairs of AE (Park Avenue and Delray) and 3 pairs of hand made Italian shoes that I got in Florence (from Quercioli, made for them). All were in the $250-300 range. The AE's are 3-4 years old and need to be sent off to be resoled, but I wore them quickly because I used to walk almost a mile to/from the metro each morning - often in them. They last a long time, and all of them can be repaired if needed as long as the leather upper is in good condition.
I don't want to pretend to know fashion, but when it comes to dress shoes, stay away from trends for every day. Square toed shoes are popular, but wearing them to the office tells me you're probably just out of college and therefore a noob to real life. If you work for a large company or are in a white collar role, stick to something more conservative. Cap toes, oxfords, that sort of thing. They never go out of style. You can have more casual or trendy shoes, but those probably aren't what you want to wear every day. It may sound contradictory at first, but a pair of trendy brown, square toed shoes with thick contrast stitching are better used to dress down a suit than they are worn every day with khakis and a polo. The former looks professional and purposeful, while the latter can look sloppy in some offices.