Winkelman was born on 3 April 1913 to a farming family in rural Missouri. She was the second-eldest of six children. She regularly fed the chickens and gathered wood for the stove. During the winter, she rode a horse to her one-room schoolhouse and would walk two miles daily in the summer.

Winkelman’s father fell ill when she was a child, and her mother had to care for him as well as six children. At the age of 15, Winkelman journeyed alone to Chicago to live with an aunt. In 1929, aged 16, she found work as a phone operator at Illinois Bell, which later became AT&T.

Following the company’s switch to dial service, Winkelman worked her way up to become a consultant, assisting Chicago businesses with their communication systems, including the police department and numerous hospitals. She worked for the company for almost four decades, retiring in 1968.

Winkelman met her husband, Lawrence “Larry” Winkelman, at a house party. The couple married on 23 August 1934. They had no children, opting instead to travel around the world and go on many cruises. She was widowed in September 1990.

By the time of her 106th birthday, Winkelman had been to 19 different countries and enjoyed 90 cruises. She had spent her 100th birthday on a cruise around Costa Rica, and was gifted 100 flowers and a 4000-strong chorus wishing her a happy birthday. As a centenarian, her hobbies included cooking and reading, as well as listening to audiobooks.

Winkelman moved to a Sun City community in Huntley, Illinois, from Arizona at the age of 100 with her friend, Robert “Bob” Gordon. She stated her secret to longevity was “moving forward.” On her 109th birthday, she described one of her key principles: “…early to bed and early to rise.”