Okay, I'm a guy who generally wears what I like. I usually search the clearance section of stores like Macy's, Kohl's, etc for stuff that looks good and is cheap. However, shoes are another story.
I usually only buy new shoes less than once a year, and usually only when my older ones are beat up. (Like they are now.) I also walk/run a lot, so I usually but whatever running/cross training shoes are the most comfortable but still rather cheap.
pity reply
I automatically suggest Converse because they come in a variety of styles and run pretty cheap, depending on what your definition of cheap is. Try to get two pairs of shoes, an everyday shoe and a more formal shoe, so it'd solve the problem of dressing up
I suggest plain white Nikes, because you can wear them with practically ANYTHING, whether you're dressing up or just having a casual day out with friends. Plus, they look clean too. :)
At payless I found some plaid Vans slip-ons that were around $20. They're not loud at all, they're pretty comfortable, and they have that casual chic thing you're looking for. Since they're not tennis shoes they can be flexible in formal situations and they're also good kicks for when you're just visiting your friends or going to the bar.
Converse ftw xD
LETS GET SOME SHOES