Though not exactly the most aerodynamic headwear for cycling, we think this cozy Little 500 dad hat is perfect for race spectators. The race itself was founded in 1951, when IU Foundation executive director Howdy Wilcox Jr. devised a charity bike race that would mimic the Indianapolis 500. From its founding to this day, the Little Five is a massive philanthropic effort that benefits the IU Student Foundation, which helps IU students in need.