The name Winnie derives from the Old English word "wyn," meaning joy, pleasure, or delight. Its origins can be traced back to the 7th century, when it was a common name among the Anglo-Saxons. Winnie is a diminutive form of the name Winifred, which also has roots in Old English and means "blessed peacemaking."

One of the earliest recorded instances of the name Winnie can be found in the epic poem Beowulf, which dates back to the 8th or 9th century. In this ancient work, a character named Wynfrith is mentioned, which is a variant spelling of Winifred.

During the Middle Ages, the name Winnie gained popularity across Europe, particularly in England and Wales. One notable figure from this period was Winnie, the wife of King Alfred the Great, who ruled from 871 to 899 AD. She played a significant role in the cultural and educational reforms of her husband's reign.

In the 16th century, a famous English explorer named Walter Raleigh had a daughter named Winnie, who was born in 1586. She was named after her maternal grandmother, Winifred.

Another prominent historical figure with the name Winnie was Winnie Davis, the youngest daughter of Jefferson Davis, the President of the Confederate States of America during the American Civil War. She was born in 1864 and became known as the "Daughter of the Confederacy" after her father's death.

In the 20th century, one of the most famous individuals with the name Winnie was Winnie-the-Pooh, the beloved fictional bear created by author A.A. Milne in 1926. The character's name was inspired by a Canadian black bear named Winnie, who lived at the London Zoo during World War I and was a popular attraction.

Another notable Winnie was Winnie Mandela, the former wife of Nelson Mandela and a prominent figure in the anti-apartheid movement in South Africa. She was born in 1936 and played a crucial role in the struggle for freedom and equality.