Social media has overtaken fashion subcultures and provide consumable aesthetics as a substitute. This leaves the idea of a personal style ambiguous and undefined with no incentive for questioning. Learning fashion history and analyzing how social media, fashion, and culture are intertwined today will encourage critical thought in one’s own self expression, content consumption habits, and relationship with social media. Ouroboros looks to define the meaning of personal style in a postmodern context, seeing what personal style means through a sociological, philosophical, and psychological lens.