I have been wearing high heels for many years and pretty much putting up with the pain. The toes are smashed together in a triangle like the bow of a boat. My toes are bent upward until I walk a few feet barefoot.
A couple of years ago I discovered Vivian Lou Insoles for high heels which, are shown in the picture below.
The clear gel pad going from the arch to just shy of the heel back shifts your weight back. It moves your weight from the ball of your foot to the heel. It more evenly distributes your weight over the whole foot.
Ice them up
Vivian Lou insoles help a great deal but the old ice trick makes high heels even more comfortable. A couple of years ago I wrote about this technique on my other site www.chicladies.org. Recently I made a discovery that makes it even better. I was getting ready to go to a Vanity Club outing in Atalanta and had two new pairs of high heel pumps to wear.
I inserted the zip lock plastic bags with the corner deep into the toe of each shoe pushing it in with my finger. Make sure that the corner is all the way in. Filled the bags about a third of the way full with water and put them in the freezer over night.
I did this three times on one shoe but the other needed a fourth time. I put them on in between to check the fit. When the water froze each night it expanded gently stretching the shoe a little each time. The high heels pictured above are satin but the ones I did multiple times were black kid and black patent leather.
Give it a try it really works!