Entertainment PHOTOS: Caitlyn Jenner then and now By amNewYork Posted on June 1, 2015 Sign up for our amNewYork email newsletter to get news, updates, and local insights delivered straight to your inbox! See Caitlyn Jenner’s changing look, from the world record-setting Olympic win in the mid-1970s to present day. Jenner, 65, debuted as Caitlyn Jenner on Vanity Fair’s cover on June 1, 2015.