This paper presents an approach to the transformation of portrait photographs to Picasso’s cubism style using deep learning and image processing techniques. We obtain the side-view face by rotating the face model constructed from a frontal portrait image 90⁰ and then replace the left half of the portrait by the side-view face. Our approach is applicable to online transformation of selfie photographs and potentially extendable to broader categories of images and artistic styles. ©2019, Springer-Verlag GmbH Germany, part of Springer Nature.