This photograph was taken before 1914. I know that for a fact..Grandpa H moved to Minnesota in the spring of 1914. Far Guys Grandpa H was in Iowa with two of his brothers, Grover and Brian. Apparently they were headed someplace with a load of melons.
Sometimes dating old photographs is difficult, I am just guessing that the littlest boy is between 10 and 12 years old, which dates this photo 1906 to 1908. Grandpa H was born in 1889, Grover in 1894, and Brian in 1896. When did little boys stop wearing knickers and graduate to long pants? Was it an age thing? :)