Take your pair of heels to a shoe repair shop if they don’t seem to be wide enough across and are squeezing your feet. This is a common problem for women with wide feet since heels are generally designed with a medium width. A shoemaker should be able to stretch the heels around the toe area to make them more comfy and wearable.
Invest in a gel or foam shoe insert, then place it onto the insole at the heel to protect the ball of your foot, which tends to need the most support. You can also use an insert that lines the entire insole from the heel to toes.
Wear a new pair of heels for an hour or two every day for a few days before you go out with them. You should get used to walking around in the heels, and stretch them out a bit at the same time to help ensure a comfier fit when you go out on the town. When it comes time to put them on, criss-cross two clear adhesive strips across each heel at the point where the top of the shoe’s heel meets your skin.
Avoid wearing your heels every day, since this can damage your feet and make wearing high-up shoes a major pain. Alternate heels with flats, sneakers or wedges so it feels more comfortable when it comes time to put your heels back on. Reserve your heels for days when you wear skirts or dresses, since you’ll need help elongating your exposed legs for those outfits.