Let me begin with some background; I am an 18-year-old student, and I have been wearing TOMS Classic shoes for about two years. I have only owned the Classics, and all of them have been purchased in black. I don't own any other shoes. I wear these casually, on my motorcycle, in my tuxedo-- all of the time. They look fantastic.

Unfortunately, they don't last me very long. I am not a very active person; I don't rough-house, or play any sort of sports, or try and work out in my new shoes (I use my old ones for that). They always develop a hole in the big toe. I cut my toenails religiously, and I can not possibly order a size bigger without them falling off while I walk.

Pros
 - They look great and are stylish
 - They support a good cause
 - They are comfortable

Cons
 - They cost $50 ($35 would be much more reasonable)
 - They wear out too quickly

They are great shoes, but I wouldn't recommend them to everyone. They are worth buying and owning a pair, even if just to try out, though, but don't expect them to replace your shoes permanently unless you are very gentle on shoes, and you have money to get new ones every three months or so.