Good point on the under shirt legnth. That is definitely a useful tip I should have included.
I do agree that some of the Cole Haan styles aren't the greatest. What you don't see in the pics is how much more comfortable some of their shoes are over a traditional dress shoe. They're noticeably more comfortable. I wouldn't spend what they're asking for just regular shoes. I'm just talking about dress shoes. Worth trying on in the store just to get an idea.
I get my casual sneakers from Amazon or Macy's. I tend to spend around $30-60 for Vans usually. As long as you're not in a rush you can wait for deals to come to you.