Nightshift workers go against the natural sleep–wake rhythm. Light can shift the circadian clock but can also induce acute alertness. This placebo-controlled exploratory field study examined the effectiveness of light glasses to improve alertness while reducing the sleep complaints of hospital nurses working nightshifts. In a crossover within-subjects design, 23 nurses participated, using treatment glasses and placebo glasses. Sleepiness and sleep parameters were measured. A linear mixed model analysis on sleepiness revealed no significant main effect of the light intervention. An interaction effect was found indicating that under the placebo condition, sleepiness was significantly higher on the first nightshift than on the last night, while under the treatment condition, sleepiness remained stable across nightshift sessions. Sleepiness during the commute home also showed a significant interaction effect, demonstrating that after the first nightshift, driver sleepiness was higher for placebo than for treatment. Subjective sleep quality showed a negative main effect of treatment vs. placebo, particularly after the first nightshift. In retrospect, both types of light glasses were self-rated as effective. The use of light glasses during the nightshift may help to reduce driver sleepiness during the commute home, which is relevant, as all participants drove home by car or (motor)bike.