Fitting shoes can be difficult. I use to fit hiking boots, running shoes can be hard to fit too. A good distance running shoe store can be a good resourse to fit shoes as they wear out lots of shoes. Running shoe stores often have machines that analyze how ones feet strike the ground and may suggest shoe structure.

I would caution against fitting shoes with toes jammed up into the toe box. I use to do that which ended up giving me two split toenails on my pinky toes. The truth is I have duck feet though. My toes are short and close to the same length making them hard to jam into a narrow toe box. You certainly do not want to hike in boots that your toes run into the end of the toe box in, as downhill will wreck your toes. Bicycle shoes may be different but I believe many of the same principals apply.