High heels are symbols of female sexuality and are “costly signals” if the risks of wearing them are offset by improving women’s attractiveness to men. From a functionalist perspective, the costs versus benefits of wearing heels may vary according to personal and contextual factors, such as her effectiveness at competing for mates, or at times when such motives are stronger. Here, we examined potential differences between women (self-rated attractiveness, dyadic versus solitary sexual desire, women’s age, competitive attitudes toward other women) and contextual variation (priming mating and competitive motives) in their responses to high heels. Study 1 (N = 79) and Study 2 (N = 273) revealed that self-rated attractiveness was positively related to orientation toward heeled shoes. When examining responses to two very attractive shoes (one higher-heel, one lower-heel) in Study 2, dyadic sexual desire, but not solitary sexual desire or intrasexual competitiveness, predicted their inclination to buy the higher-heeled shoe. In Study 3 (N = 142), young women chose high heels when primed with free choice of a designer shoe (95% CI [53.02 mm, 67.37 mm]), and preferred a heel 22 mm (0.87”) higher than older women (Study 4, N = 247). Contrary to predictions, priming mating or competitive motives did not alter women’s preference toward a higher heel (Studies 3 and 4). Our studies suggest that attractive women augment their physical appeal via heels. High heels may be a subtle indicator of dyadic sexual desire, and preferences for heels are stronger at times in the lifespan when mating competition is relatively intense.