There is provided a display control device including a matching section configured to match a first image or sensor data output from a first imaging device or a sensor worn on a head of a first user, to a second image output from a second imaging device worn on a part other than the head of the first user, a sight estimation section configured to estimate a region corresponding to a sight of the first user in the second image, on the basis of a result of the matching, and a display control section configured to generate an image expressing the sight of the first user using the second image on the basis of a result of the estimation of the sight, and display the image expressing the sight of the first user toward a second user that is different from the first user.