This Major Research Paper explored the evolution of professional profile pictures, the influencers who determined original profile pictures, and the historical trends we continue to see in current professional profile pictures. Applying social identity theories, brand theories, and the study of facial appearances, known as physiognomy, this thesis explored professional profile pictures of multiple professions including journalists, faculty and staff at Canadian postsecondary education institutions, photographers, and a career coach. Applying an autoethnographic approach, this thesis is an initial conversation about the systems that created the professional profile picture and the trends that ensued.