Alexander was born in Greene County, Tennessee, the son of William and Maria Henshaw Alexander. Soon after 1850, the Alexander family migrated north into Tippecanoe County Indiana near Romney. In 1857, Maria Alexander died and was buried in the Romney Cemetery. Sometime soon after Maria’s death, William and his younger children migrated west to Harrison County Missouri. Although it is not known where James F. Alexander was during the 1860 census it is probable that he remained in the Tippecanoe County area after his father moved west. He enlisted in the 150th Indiana Infantry from Tippecanoe County in 1863 and mustered out in August 1865. He was married in Decatur, IL in 1868, to Alma Waite. In 1870, he and Alma were residing in Champaign, IL and his employment was listed as a cabinet maker. Their first son William C. Alexander was born in Decatur or Champaign in 1869. His second son James Frank Alexander was born in 1874 and it is believed the family returned to Tippecanoe County soon after that. In 1880, he is listed on the census record as an architect.
Alexander trained in St. Louis before receiving a degree in architecture from the University of Toronto. He is believed to have begun his career with a brief stint in Chicago before returning to Lafayette and establishing his own practice there. Alexander gained local popularity as a designer of offices, schools, and civic buildings. He supervised the construction of the Tippecanoe County Courthouse, his most high-profile commission, in 1882.
Although he primarily worked in Indiana, Alexander was very active in the Western Association of Architects (WAA) and as such made contacts among his colleagues throughout the Midwest. As a member of the WAA, he served on committees within the organization alongside the likes of Dankmar Adler, John Root, and Daniel Burnham, in the years just before the construction of Hillcrest. He continued to serve in the WAA through its consolidation with the American Institute of Architects (AIA) in 1889.
The year 1892 was an eventful one in J.F. Alexander’s professional life. From that year onward, Alexander restyled his firm as J.F. Alexander & Son to include James F. Alexander, Jr., who had recently completed his own architectural training. It is possible that Hillcrest was one of the younger Alexander’s first professional projects, though no existing documentation outlines his precise involvement in the design and construction of the house. The firm also received the commission to build the Indiana State Fairgrounds in Indianapolis in 1892. In October, when Hillcrest’s construction phase was well underway, AIA President Richard Morris Hunt nominated Alexander to several committees within the national organization at the annual meeting in Chicago. Alexander also designed the now-demolished Knights of Pythias Building in Indianapolis in 1905, a stately flatiron building which predated its more renowned New York counterpart (designed by AIA colleague Daniel Burnham) by two years.
As early as 1915, the Lafayette City Directory lists the firm’s name as J.F. Alexander & Sons, implying that his youngest son, William C., also joined the family business. The city’s 1918 directory cross-references Alexander’s firm with that of Riedel & Zink, which succeeded the former and went on to design many buildings and funerary monuments in and around Lafayette. The succession likely came as a result of the deaths of J.F. Jr. in 1917 and William in 1920. According to an obituary, the elder Alexander relocated to Springfield, Missouri, to live with a nephew circa 1912, and he died in that city at age 82, ten years later.