The 'CEO of Swag' meme stems from the broader 'CEO of' trend that dominated social media platforms like TikTok and Twitter starting around 2019. This format involves crowning someone the absolute authority over a specific, often absurd, characteristic or vibe. The 'CEO of Swag' specifically highlights individuals who exude extreme confidence, wear flashy outfit combinations, or pose in stylized ways that evoke early 2010s internet culture. It is frequently used both unironically to celebrate unique style and ironically to poke fun at over-the-top displays of bravado or intentionally 'cringe' fashion choices that are so bad they become good.