I don't usually wear high heeled shoes because they're so uncomfortable. I have a few pairs that have ~2" heels, but the heels are big and chunky to provide more comfort and stability. Here's an explanation of why high heels = pain from the MIT website:
"All podiatrists know the problem with high heels. Standard construction of the shoes creates a 'ramp effect' with the foot sliding down toward the toe box placing continuous pressure on the digits and ball of the foot. Bunions, hammer toes and a painful thickening of the nerves between toes are the all too common result. To add insult to injury, when the ankle flexes to accommodate the tip-toe position, the joint becomes inherently unstable and the knee joint overcompensates frequently leading to a syndrome of knee and back pain."
Fortunately, there's a company called Insolia that is pioneering shoe archicture redesign. The inventor behind the concept, Dr. Howard Dananberg, has "created formulas for unique, curved profiles of the insole board of shoes that would put the foot in optimal position and alignment at each specific heel height resulting in the distinctive--but outwardly invisible--'cup and bump' of shoes with Insolia." With their technology, the increase in forefoot pressure from wearing conventional two-inch heels compared to wearing sneakers decrease from 64% to 22%.
Not many stores/brands carry Insolia yet, but I noticed that Millie's in Hong Kong does. Hong Kong - one of the few places in the world where I can find shoes that are small enough to fit me... but that's a whole other story. I'll be sure to check them out when I'm there this Christmas.