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Danger ranking: 5. We knew they weren't orthopedic shoes, but Brenner says stilettos are even worse than we thought: "Intense pressure on the front of the foot can lead to things like sesamoiditis, which is inflammation of the tiny bones under the big toe, and metatarsalgia pain, caused by pressure under the toes. Tight shoes that squeeze the toes together can lead to neuromas, or thickened and irritated nerves. Use caution when wearing shoes higher than two inches, especially for longer than two hours. We see a lot of lateral ankle sprains caused by stilettos," says Brenner. She adds this caveat: "Choosing footwear is like dieting: You can wear anything in moderation."