I've seen some custom shoes out there and decided to give it a try. I custom designed the shoes on the Converse website using their "Create" feature and even had them stitch "Luna" onto the back. Once the shoes were created and delivered, the hard part started; painting her cutie mark onto the back heel of each shoe. A friend of mine helped me create the moon template and a custom mix of dark blue fabric paint as the base / cloud foundation. Since the back portion of these shoes is so small and I knew I'd only get one shot to get it right I ended up sacrificing an older pair of chucks to test out the template and fabric paint.
Once I had the process down I got busy creating the real pair. It took me about two hours to get both shoes painted, I made myself go slow to ensure I had nice clean lines and to avoid paint bubbles and any unnecessary paint buildup. When I was waiting for the shoes to be delivered I happened to stumble across shoe wings at a local party supply store. They were originally a very shiny royal blue color, but I went to town painting them and I think the end result looks pretty kick ass. (The wings can be removed)
I ended up wearing these to Comic-con a few weeks ago and wear them to work, without the wings since it's an office environment regularly.
Since these turned out so well I am currently kicking around design ideas for either a Scootaloo pair or perhaps Nightmare Moon and or Twilight Sparkle. Either way I am pleased with the results and hope this helps inspire others to create their own custom MLP shoes.