Male sexually selected signals can indicate competitive ability by honestly signaling fitness-relevant traits such as condition or performance. However, behavior can also influence contest outcomes; in particular, boldness often predicts dominance rank and mating success. Here, we sought to determine whether male ornament size is associated with consistent individual differences in boldness in water anoles Anolis aquaticus. We measured the relative size of the dewlap, a flap of skin under the chin that is a sexually selected ornament in Anolis lizards, and tested for associations with responses to a novel and potentially risky environment: time to emerge from a refuge into an arena and number of head scans post-emergence. We found that individuals consistently differed in both time to emerge and head scanning (i.e., individual responses were repeatable), and that dewlap size was negatively related to number of head scans. This suggests that ornament size could indicate male boldness if scanning represents antipredator vigilance. We found that males that had larger relative dewlaps were also in better body condition, but boldness (i.e., head scanning) was not related to condition. Lastly, we found consistent differences in behavior between trials, showing that anoles were becoming habituated or sensitized to the testing arena. Overall, our study shows that in addition to indicating condition and performance, dewlap size could also honestly indicate male boldness in Anolis lizards.