On April 9, 1865, General Robert E. Lee, the commander of Confederate forces, surrendered to General Ulysses S. Grant, commander of the Union forces, at Appomattox, Virginia.  Davis believed that a guerrilla war could still be fought, but Lee and General Joseph Johnston rejected the strategy as futile.  Davis's wife, Varina, and children had already left the Confederate capital of Richmond, Virginia, on March 27, and the Confederate president set out on the evening of April 10 to join them in Greensboro, North Carolina.  The Davis party continued southward toward Florida, where they hoped to catch a boat for Texas.  Once there, Davis would direct the continued fighting of the Confederate troops under General Kirby Smith.  (Later, on June 2, 1865, Smith's Trans-Mississippi Department was the last Confederate force to surrender).

At the break of dawn on May 10, the Davis encampment outside Irwinville, Georgia, was awakened by gunfire.  Union cavalry troops were seen approaching in the distance, and a pleading Varina Davis finally convinced her husband to escape while he still could.  Inside the darkened tent, Jefferson Davis put on what he probably thought was his overcoat and departed for a nearby swamp.  He had accidentally donned his wife's raglan (a cloak-like overcoat).  Mrs. Davis threw her shawl over his head to obscure his identity, and then sent her female servant with a bucket to walk with her husband as if they were fetching water.  

The Union soldiers probably thought at first that the two figures were both women, but then a corporal noticed the spurs on Davis's boots.  The corporal rode over to the two, and pointed his gun at Davis, asking his identity.  The Confederate president considered lunging at the federal officer and making a break for it, but his wife ran to her husband and threw her arms around him.  The soldiers soon realized whom they had captured, and the Davis party was escorted to Macon, Georgia, the headquarters of General James Wilson, the Union commander of the region.

From Macon, Jefferson Davis was transported to Fort Monroe in Virginia.  The arresting officers had not reported anything unusual, but gossip soon spread among soldiers not on the scene that Davis had been wearing women's clothing when he escaped.  By May 13, the rumor had reached the ears of Edwin Stanton, the Secretary of War.  He obtained "eyewitness" accounts from men who wanted part of the $100,000 reward money offered for Davis's capture, and passed word of the incident along to the Union press.  Stanton recognized that the story, which threw suspicion on Davis's masculinity and bravery by depicting him as a cross-dressing coward, was an excellent opportunity to humiliate Davis and thus undermine any attempt to portray him as a hero or martyr.

On May 23, to gain more credence for the story, a U.S. army officer ordered Mrs. Davis to hand over her raglan and she innocently complied.  When he returned the next day for her shawl, she was suspicious of his motive but forced to surrender the garment.  Davis himself had already heard whispered remarks about his womanly flight, and both he and his wife soon saw the newspaper articles and cartoons. 

When Stanton viewed the clothing, though, he knew it would not be helpful for propaganda purposes.  Mrs. Davis's raglan was not only nearly identical to her husband's, but was similar to the standard raincoat worn by Union soldiers.  The shawl, too, was not unlike that worn by many men of the period, including the late President Abraham Lincoln, to keep warm in the poorly heated buildings of the day. Stanton therefore had the garments placed in a War Department safe, where they remained for decades.  

The War Secretary slightly altered his account of Davis's capture by stating that the former Confederate president tried to flee while wearing a woman's coat and shawl, but not a dress.  The Northern press, however, continued to depict Davis in hoop skirt, petticoat, and other clearly feminine articles of clothing.  Davis was mortified by the false accounts, and it added to his depression during his two-year incarceration.