In Mindy Kaling's book "Why Not Me?", the author paints a vivid picture of Doug, who embodies a specific trend of success during the mid-2000s. His wardrobe choices, featuring an Affliction waffle-knit tee and True Religion jeans, signify a certain status and lifestyle associated with that era. Kaling's mention of this attire highlights how clothing can reflect personal achievements and cultural trends.

This detail not only characterizes Doug but also evokes nostalgia for the fashion of the time, showcasing the intersection of personal identity and societal perception. Through this description, Kaling effectively captures the essence of a moment in time, allowing readers to relate to the notion of success as portrayed through style and fashion cues.