Cabinet photograph of a young man identified as Henry T. Stiff, Class of 1891 at B.H.S., which might refer to Brockton High School at Brockton, Massachusetts.
The photograph was taken by the Munroe and Stiff studio of 64 Warren Street, Boston, Roxbury District. Henry's father Thomas P. Stiff was a photographer; it must have pleased him to take his son's graduation photograph.
From online research, hopefully correct: [corrections welcome]
Henry Thomas Stiff was born 9 January 1873 at Carleton, Ontario, the son of Thomas P. and Charlotte Amelia (Keith) Stiff, who were born at Osterville, Massachusetts, and Middleborough, Massachusetts, respectively.
Thomas operated a photography studio at Ottawa, Ontario, with his brother Philander, for a few years in the 1860s and 1870s. He's listed in the 1871 Census of Canada at Ottawa.
Henry's younger brother Walter was born in Canada about 1876/77. The family returned to Massachusetts not long after that. They were enumerated in the 1880 Census of Taunton, Massachusetts.
On 14 April 1897, Henry Thomas Stiff married Bessie Cary Packard, daughter of James Willard Packard and Mary Alice (Cary) Packard. Bessie was born about June 1873 and died about seven years after her marriage, on 1 February 1904 at Brockton. I don't believe they had any children.
On 5 November 1905 at Brockton, Massachusetts, Henry married Bessie's younger sister Alice Marie Packard, who was born about March 1883.
They raised a family of at least three children at Boston, Massachusetts, where Henry was a civil engineer. By the time of the 1920 Census, Alice Marie (Packard) Stiff had died and left Henry a widower again.
If you have any corrections to the information above or any insights into the Stiff and Packard families, please leave a comment or contact me directly.