An experimental investigation was conducted to calculate the aerodynamic drag on a cyclist wearing different types of clothing. The different outfits worn for this experiment were a professional skinsuit, a professional cycling kit, a t-shirt and shorts, and a long-sleeved flannel and jeans. The aerodynamic drag was ultimately found using the coast down method, a process in which a cyclist increases their speed to a chosen maximum threshold, and upon reaching this speed, ceases the pedal stroke and maintains the aero position until the bicycle comes to a stop. The data was gathered using an AeroPod, speed sensor, and GPS unit. The data gathered was imported into Excel for data analysis. The average CdA values at race speed (26-30 ft/s) for the skinsuit, cycling kit, t-shirt and shorts, and flannel were calculated to be 4.180 ft2, 3.668 ft2, 4.884 ft2, and 4.223 ft2, respectively. These race speed averages were found using data from three separate Ironman Triathlons. The cycling kit was found to be the most aerodynamic at the race speed. The results of this study reveal that cycling apparel can only be optimized for a small range of speeds and cycling outside of this optimal range delays the initiation of the reduction of boundary layer separation, thus resulting in more critical time spent in the flow transition region. The skinsuit’s performance was more aerodynamically efficient than the cycling kit at speeds greater than 36.8 mph. The cycling kit is more aerodynamic for speeds slower than 36.8 mph. The slickness of the skinsuit was found to be detrimental to the cyclist’s aerodynamic drag, as the lack of roughness on the skinsuit prevented the initiation of turbulent flow, which results in a decrease in drag. Overall, the experiment confirmed the hypothesis that a cyclist is more aerodynamic when wearing cycling apparel as opposed to casual, loose-fitting clothing.