Jessamine (Jessie) McFarland was born in 1878 and was the sixth child of Dr. Thomas Jefferson McFarland (a Civil War veteran) and Caroline Pauline Jayne. Her siblings included Marion Minter (Buddie), Mary Pauline (Sissy), Van Earl, and Juliet Jayne (Lulie). Jessamine went by Jessie, she had no middle name, but growing up she would often use Jessie Jayne at tea parties with her friends or to sign a letter. She and her siblings grew up in Port Lavaca, Texas.

At 18, Jessie attended Sam Houston Normal Institute in 1896 to receive a teaching certificate. There she met her lifelong friend Daisy Thorne. Jessie and Daisy were expelled from SHNI two times during their one-year study. Their first expulsion was due to a double date with brothers on the "do not date list." Their second expulsion was due to stealing a horse and buggy on Huntsville's Main Street for a short joy ride. For each expulsion they were sent back to their families by train but returned to campus with their parents to argue readmittance. They were granted readmittance each time, but their second expulsion was considered their "final warning."

Jessie graduated from SHNI on Tuesday, June 1, 1897, receiving her First Grade Certificate. She taught for one year in Port Lavaca, Texas.

In 1904, Jessie married Franklin "Frank" Potter Penfield, a civil engineer. Jessie and Frank and two daughters, Elsie Penfield and Carolyn Jayne Penfield.

Two of her great-grandchildren attended Sam Houston State University, Diane Gundelach and Jan Gundelach. Diane graduated from SHSU, while Jan graduated from Texas State University. Before Jan transferred, she witnessed Old Main burning from her dorm window. Old Main was considered to be Jessie's favorite building.

Jessie lived her last years in Columbus, Texas, until her death in 1954 at the age of 76.