Is it just a matter of trial and error (it seems I have tried 100 pairs) to find flats that stay on when you walk and do not gap out at the sides?

I have to resort to mary janes with the strap near my toes so far because I have not found flats that stay on. When i go down a size my toes seem scrunched.

I would be in heaven if I found flats that:

1. did not slip off when walking

2. gave my toes enough room

3. had room for orthotic

4. looked smart casual

Is this too tall an order?