Previous owner said he wore them around a dozen times, but probably a bit more than that. You can gauge it based on the condition. I wore em under 5 times before accepting that they were to small for me. I wear a 9 in converse and 9.5 in most other shoes and they were a bit too small. If you're an 8.5 or probably even up to a smaller 9 they'll probably fit you. There are raw denim stains on the interior of the tongue, but it doesn't effect how they actually look. You can see there's some wear on the suede on the toe, but other than that the shoes aren't that worn. The actual leather is in good condition, there's just a little dirt on it. I don't know how to best clean it, so I left it as is. The shoes come with the shoe bags and in the original box. The box is not in mint condition, the lid is a little torn. Just how I got it, couldn't do anything about . The $190 includes shipping and paypal fees, shoot me an offer though and we can talk about it.