Bicyclists risk being involved in collisions with motor vehicles, even during daytime. Thus, bicyclists who ride in daylight must enhance their conspicuity. This study assessed the daytime conspicuity benefits of bicycle taillights using eye tracking technology. Participants were driven along an open-road route while wearing an eye tracker and pressed buttons when they detected and recognized a test bicyclist. Participants encountered the bicyclist displaying one of four taillight configurations, and the distances from which they responded to the test bicyclist were recorded. The results revealed that, after participants first glanced at the bicyclist, a significant amount of time was needed to detect and recognize the bicyclist. Further, seat post-mounted lights displayed with or without lights mounted to the heels of the rider’s shoes provided the greatest conspicuity advantage in terms of recognition. This experiment offers useful insights into the optimal light placement options for bicyclists to enhance their daytime conspicuity.