The pain you are describing is what I had, which is the 5th metatarsal being compressed. Since that part of your foot spreads along with your little toe if your toe doesn't have enough room it will cause discomfort. That is why I said narrow toe box. That's why I also recommend you talk to your podiatrist with your shoes so they can tell you what they think. I know what causes my foot pain. Also, my podiatrist happens to be a cyclist.