A high heeled shoe and shoe sole insert are provided that are configured to provide relief from the forces on the foot created by walking in high heels. The shoe comprises a layered sole having an outsole, a midsole, and an insole. The midsole of the shoe comprises a cutout that is positioned over the metatarsal pressure point of the user's foot when positioned within the shoe. The cutout is filled with a shock absorbing material, such as Ethylene-vinyl acetate (EVA) foam, and includes a layer of paperboard for further cushioning. The shoe sole insert similarly includes a metatarsal padded region and a medial longitudinal arch pad to provide a layer of cushioning above the midsole of a user's footwear. The present invention provides relief while wearing high heels by cushioning the user's foot in high pressure zones, thereby relieving the pressure and reducing injuries or soreness.