I think it looks like the middle bone in your toe is missing. I had a friend that had a similar problem with almost all of her toes and I believe the solution was that they were surgically broken so it kind of relieved the pressure of being squished up to her foot. Sounds like a horror story, but it really helped her no longer have pain when wearing shoes.

My friend recently got married and bought a pair of heels for the wedding and then a pair of flats for the reception.