Although mayors can have important impacts on citizens’ daily lives, local politics remains understudied, especially compared with national and regional politics. This study focuses on Canadian mayors’ digital political gender performance—or self-presentation—on Facebook, Twitter, and Instagram and the context in which this gendered performance arises. Overall, results confirm that mayors’ gendered performances are on a continuum rather than binary. Results from a visual content analysis of nine Canadian mayors’ social media accounts show that, broadly speaking, women mayors gravitate toward congruent, mixed gendered performances and avoidance strategies, whereas men mayors also display mixed performance of their gender, while more freely exploring congruent and incongruent approaches to gendered stereotypes. Additionally, semistructured interviews with these mayors show that women mayors still work under added constraints because of their gender, which translates into comments on their appearance, attitude, and lifestyle choices; increased aggression and lack of respect; and a generally greater mental load.