William Tomlin Iowa City

The man on the left is William Tomlin. I am trying to date the photo because there is a william Tomlin Jr. AND Sr. I'd like to know this one . Senior was born 1865 died 1931 and Junior was born 1890 died 1941. The photo is marked "Jas. Luscombe Cottage Gallery Iowa City Iowa" Are there any experts out there that can date this picture??????
People in photo include: William M Tomlin