The relationship between everyday light exposure and sleep was studied for office workers. The study was conducted during the upswing of the COVID-19 pandemic, enabling a comparison between Office and Home Workdays. Fifteen full-time office employees were monitored for a period of 4–6 weeks. They wore a light-tracking device on their clothes and had a sleep tracker at home. Compared to an Office Workday, light exposure was lower in the afternoon and total sleep time was almost 5 minutes longer on a Home Workday. Sleep efficiency was the same on both workday types. A higher median illuminance level in the afternoon was significantly related to later sleep onset on an Office Workday. Higher median illuminance levels in the morning were related to earlier awakening. Counter to expectations, higher light levels in the evening were also related to earlier awakening. Everyday light exposure matters for sleep quality but may affect circadian functioning differently than the often more extreme light interventions employed in laboratory experiments. Moreover, differences in outcomes between Office and Home Workdays signal the need for further investigation to provide supportive light levels during workhours.