Olsen earned her private pilot's license after pursuing flight from a young age. She joined the WASPs the year they were established.
5 facts about the nation's first female Air Force pilots
She flew 61 missions for the Sixth Ferry Group in more than two dozen different planes including P-38s, P-51s, and B-17s, according to The New York Times. More recently, she was a dance instructor.
"She was qualified on everything the Army flew, as well as some Navy planes," Kim Olsen, Dorothy Olsen's son, told the Air Force. Her favorite planes to fly, he shared, were P-51 and P-38 fighters.
"She felt bombers were like driving busses," Mr. Olsen said.
Q&A: This author says the WASPs she met are 'feisty as ever'
At 92, Olsen met Capt. Jammie Jamieson, an F-22 Raptor pilot. Olsen read a feature article on Captain Jamieson and requested the opportunity to meet with her. At that meeting the two pilots swapped stories.
"I loved every minute of it," Olsen told Jamieson.
At the time, WASPs weren't recognized as military personnel — they risked their lives without any of the military benefits their male counterparts were offered. It wasn't until 1977 that they received veterans' benefits. In 2010, they were collectively presented the Congressional Gold Medal.
Olsen passed away at her home in University Place, Wash. on July 23.