Bessie Wallis Warfield was born at a resort in Blue Ridge Summit, Pennsylvania, on June 19, 1895, or June 19, 1896, to Teckle Warfield, a bank teller for the Continental Trust, and Alice Montague. There is much controversy about Bessie Wallis's actual birth year, which some say was obscured to protect her parents from the social stigma attached to having a child out of wedlock. There is no birth certificate for Bessie Wallis. Her father died only five months after her birth from tuberculosis, forcing Alice to depend on the more wealthy members of the Warfield family to support her and Bessie (who later convinced everyone with the exception of her grandmother to call her Wallis). Wallis grew up in Baltimore, living with her grandmother and her Uncle Solomon. She first attended Miss O'Donnell's School in Baltimore, and then at about age ten she attended Arundell, an all girls school in Baltimore. Wallis was a 1914 graduate of Oldfields, another all girls school north of Baltimore.

In 1916, Wallis's visited her cousin, Corrine Mustin and her husband Navy Captain Henry Mustin in Pensacola, Florida. There she met her first husband, Earl Winfield Spencer Jr., a U.S. Navy pilot. Warfield and Spencer were wed November 8, 1916. Their marriage was rocky; Earl was an abusive alcoholic. When Spencer was sent to fight in the Far East, the two grew apart. Wallis went to visit Spencer Jr. overseas in an attempt to save the marriage, but it only confirmed that the marriage was over. After 11 years of marriage they divorced in Shanghai on December 10, 1927.

Wallis later remarried Ernest Aldrich Simpson, an English American shipping contractor who divorced his wife, Dorothea Parsons Dechert, to marry Wallis. They were married in London on July 21, 1928.

In 1930 the Simpsons were asked to chaperone a weekend at a friend's hunting camp in the English countryside. Among the guests was Edward, Prince of Wales. This was Wallis's first formal encounter with the prince.

Over the next four years the Simpsons were engaged in numerous high society functions. The Prince became a regular visitor to their London flat and they to Fort Belvedere. Despite the social success of the Simpsons, their marriage was in turmoil. As they divorced, the affair between Wallis and the Prince became more and more visible. In January 1936, King George V died and the prince became King Edward VIII. Wallis's second marriage had officially ended in October of that same year. As pressures mounted from the media and the English government, Wallis fled the country as the king was faced with the decision of abdicating the throne. The Royal Family, along with the British government, was against Edward marrying the twice-divorced American since the British monarch is also Supreme Governor of the Church of England. Until 2002, the Church of England prohibited the re-marriage of a person whose former partner is still living. The soon-to-be Duchess was also suspected to be carrying on affairs with other men while engaging in her romantic relationship with Edward VIII. Wallis was continually accused of being a money grubber and a woman whose sole desire was to take advantage of the Prince's power.

In December 1936, King Edward put an end to the controversy by abdicating the throne and famously stated; "I have found it impossible to carry the heavy burden of responsibility, and discharge my duties as King as I would wish to do, without the help and support of the woman I love." The couple married in France on June 3, 1937. They lived in France as the Duke and Duchess of Windsor—the title of "Duke" was granted prior to the wedding by the new king, King George VI.

The Windsors lived a wealthy yet nomadic life due to their disapproved marriage by the Royal Family. Before and into start of World War II, the Duke and Duchess lived in France. At the beginning of the war the Duke was stationed with the British Army in France. In May 1940 Germany invaded northern France and the Windsors fled south, first to Biarritz, then in June to Spain. Both the Duke and Duchess were criticized as Nazi sympathizers. Before the war, they were the guests of Adolf Hitler. And as the war continued the Duchess was accused of leaking secret information to the German government. As a result, at the command of King George VI, the Windsors were sent to the Bahamas where the Duke was appointed governor. Winston Churchill, then the British Prime Minister, felt by placing the Duke in the Bahamas would lessen the risk of the Duke and Duchess from further leaking information that was detrimental to the British war efforts.

After the war the couple continued to live in France where they spent their comfortable retirement. The Duke passed away in 1972. Although the Duchess was very frail she attended his funeral; this was her last formal appearance until her death. The Duchess died April 24, 1986, in her home in Paris after a prolonged illness; she had fallen into a vegetative state and her heart had eventually failed.

The Royal Family had a great distaste for the Windsors; naturally it was Wallis that struck the deepest nerve. The Royal Family prohibited the Windsors to reside in England. By letters of patent, the Duke was permitted to be addressed as "His Royal Highness," but the address "Her Royal Highness" was specifically prohibited for the Duchess. She instead was to be addressed as "Her Grace." Wallis was never invited to stay a Buckingham Palace, except at the Duke's passing for his funeral in 1972. At the Duchess's death the court was not in "official mourning." Only the royal family would observe a period of mourning. At her own funeral, her name was not mentioned at all; the only reference made to her during the entire ceremony was by The Cannon of Westminster, as "our sister."

Almost one year after the Duchess' death on April 4, 1987, a two-day auction was held in Geneva. The auction could have been compared to a Red Carpet event, with celebrities rolling in by limousine with large checkbooks. The two-day event yielded over 50 million dollars. The biggest items were van Gogh's "Sunflowers" selling for $39.9 million and a Royal Navy officer's sword inscribed "To Edward Prince of Wales Lieutenant R.N. From His Affectionate Father George" sold for a record breaking $1,466,653. The largest individual buyer was Alexander Acevedo from New York spending a total of $4.26 million. The auction concluded with a total sale of $50,281,887.