Note: I only looked through the threads from last December until the present, so I am truly sorry if I missed something earlier than that on a pertinent related subject. I am looking to start investing in my shoes, rather than paying $50 for something uncomfortable that I won't want to wear next season. I have two major problems, though: my medical problems and shoe size. I'd love to have help from the resident shoe experts so I can stop looking cute until your eyereaches my shoes! I'm looking for a comfortable pair of cute yet basic heels that meet the following characteristics: 1. Timeless 2. Comfortable 3. Sturdy. No stiletto heel since I often have balance issues due to my health. I need heels that feel like flats. 4. Will fit a wide foot. (Not just sort of wide. Very wide) 5. Looks like it was designed for someone not in orthopedics (which is the case with a ton of wide shoes). I've been searching all over and have been empty handed. I've been looking at the Cole Haan Nike Air pumps, but the only ones I can smoosh my foot into are open-toed. That's not going to get very far this winter. Thanks for your help!