How wrinkled can your shoes get before you should replace them? My loafers have deep creases from left to right, but are very comfy and the soles are in good shape. Esthetically, where do you guys draw the line about shoes being worn out, so to speak? Edit: or, is there a way to remove wrinkles from leather shoes? I already use shoe trees. Really depends on the shoes... if they are made of good leather and are developing character that's one thing, if they are cracking and starting to fall apart that's the other end of the spectrum. Post pics I guess. also, assuming they aren't crap, some leather conditioner can help soften them up and keep them from cracking etc.