A custom orthotic can absolutely be worn in a dress shoe. Men are usually able to fit the same orthotic that they use for a running or tennis shoe into their dress shoes. Because of the vast difference between an athletic shoe and a woman's dress shoe, a different orthotic is often necessary for women. An orthotic for a woman's pump, flat, or hi-heel will be thinner, narrower, and more flexible to allow both the orthotic and the foot to fit comfortably into the shoe.

The main criteria for an orthotic fitting into a dress shoe is that the back of the shoe, or heel counter, is closed. An orthotic does not work well in a sandal, clog, mule, or slide, unless they are made specifically to hold an orthotic.
Dr. Andrew Schneider
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A podiatrist and foot surgeon in Houston, TX.