But you don't have to swear off high heels altogether. It's possible to make high heels more comfortable. Just pay attention to how much lift you're getting. “Two inches is my cut-off,” says Ward. “A heel below that height does not add significant stress to the metatarsals as the weight can remain distributed between the heel and forefoot.” This also helps you stay balanced (read: no wipe-outs) in your kicks, she notes.
Heels with a square, open, or round toe are going to be much more comfortable than a narrow, pointy toed heel. Pointy toed heels smash toes together and compact the ball of the foot making it much more likely that you’ll experience discomfort quicker. This is especially true if your feet are on the wider side. If you know you’ll be standing a lot, opt for a square, round, or open toe shoe.
You should always choose heels with thicker souls because that will ensure that you have enough ground to land your feet on. The ground will give you ample space to your feet and you will feel comfortable walking in them. Your legs can be hurt by thin soles because they put more pressure on your feet and dirt and other external agents can get into the legs and make your feet dirty and cracked.
This secret to reduce pain while wearing heels is so good, you’re going to want to share it. Woman’s Wear Daily recommends taping your third and fourth toes (counting from the big toe) together to alleviate pain from wearing high heels. Sound crazy? The proof is in the science: there’s a nerve that splits between those two toes, which causes pain when pressure is put on it (like when you wear heels). The tape helps to remove strain on the nerve. 
I’ve heard people argue that my new, near-daily ritual is ridiculous, that no shoe is worth that much pain or effort. But how different are heels from other small rituals we undertake every day, such as applying makeup? The payoff in terms of the confidence I feel when stomping down the street in a pair of killer heels is worth way more than the extra 30 seconds added to my morning routine.
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