That Hat
Brady continued his long hair trend into the 2011 season. However, eyebrows arose when he attended the Kentucky Derby. The quarterback’s fashion choices became a topic of conversation. His long hair fell beneath a Panama hat and he also wore a questionable suit. We applaud the audacity of his decision-making but it didn’t age well.

This is the face of the most confident man on the planet. Most ordinary Americans wouldn’t dream of wearing this look because they wouldn’t pull it off. In truth, Brady doesn’t succeed either but he’s the greatest quarterback of all time. Whenever people mention Brady’s hat, this is what they’re talking about (via Boston.com).