Heel pain usually after going from heels to barefoot but still hurts if also wearing flats?

Plantar Fasciitis: Wearing heels frequently can cause a tightness in the achilles tendon. If you have to wear heels daily you should focus on achilles stretching exercises. Try otc soft orthotics which may fit in you dress shoes and more importantly your flats. Avoid barefoot walking. If these conservative approaches are not adequate then see a podiatrist for cortisone injections and/or custom orthotics.

Yes, flats are worse: Heel pain is caused by inflammation of your plantar fascia which is a band that spans your arch. When you go barefoot or wear flats, that band is stretched to the max and will cause pain. Shoes with heels will decrease the stretching of that band and usually are more comfortable. The solution is orthotics in flat shoes to support your arch and prevent stretching of the plantar fascia.

Arch support: Wearing high heels can cause abnormal pressure distribution to your forefoot leading to potential problems. Shoes with improper support may be one cause of your foot pain. Try wearing properly fitting shoes with good arch support.