This story may seem shocking and little sad to some who are romantically inclined to the modern myth about the Tear Dress. The myth is that our women wore this style of dress at the time of the Trail of Tears in 1838-39. That is not true for two reasons.
First of all, Cherokee never had a traditional style of dress that was unique or ethnically different than any other tribe in the hot and humid Southeastern United States. The clothing of both sexes, as described by the very earliest European adventurers, was primitive and scant, covering mostly their private parts, and made of mostly animal hides and furs. They did use a rudimentary form of finger weaving and netting to make sashes, belts and rope. Loom weaving technology, which would allow them to make piece goods, was not available until the opening of the frontier to missionaries, the Moravians in particular.
The clothing they made was fashioned on the type of clothing they were taught to make plain, simple and utilitarian. Frontier fashion was nothing like those seen in picture books and paintings of the ladies in eastern sea coast cities such as Boston, Philadelphia or New York. The second reason that the Tear Dress could not have been worn at the time of the Trail of Tears is because the style is completely wrong for the period. Women’s fashions of every historical period have a very definite silhouette, related primarily to the rise and fall of the waistline and the shape and size of the skirt.

In the late 1830’s, the period of the beginning and the end of the Trail of Tears episode, women of fashion in the cities along the eastern seaboard were wearing garments that costume historians call late Empire, Romantic period, or Early Victorian. The Tear Dress is definitely a style that came into fashion at a later date. There is one painting extant of a Texas Cherokee couple which shows the woman wearing a most definite "Empire" style gown – high waist, bell shaped skirt and short puff sleeves. Whether this painting was executed on site with real Cherokees as models, thus recording a moment in time, or was finished by the artist at a later time, and using another model in city-fied clothing. It was not uncommon for artists to use substitute models when painting Indian subjects.

The first official tear dress was made for and worn by Virginia Stroud during her reign in the titled position as "Miss Indian America" 1969. The garment we call the Cherokee Tear Dress came about to fulfill the needs of a particular situation and had more to do with embarrassment than it had to do with tribal pride or tradition. The situation arose in 1968 when a young Cherokee woman, by the name of Virginia Stroud, was chosen as "Miss Indian America". She had competed and was crowned in a Kiowa buckskin dress she had borrowed from a college friend.
W.W. Keeler, who was the appointed Cherokee Chief at the time, was approached by a group of Cherokee women about Virginia Stroud’s official wardrobe. They felt it was unacceptable for a Cherokee women who was suppose to be representing the Cherokee people in the public eye was appearing at public events dressed as a Kiowa. Chief Keeler agreed and appointed a committee of Cherokee women to find something more appropriate for Miss Stroud that would reflect the Cherokee’s eastern woodland traditions, history and style.

They could not find an established precedence in Oklahoma for a traditional tribal dress. The answer they decided could only be found someplace in North Carolina, Georgia or Tennessee. The ladies mounted a serious search for a record of a dress design that would be uniquely Cherokee and acceptable by Chief Keeler. They did not want to simply copy or adapt any other tribe’s style. And they did not want the dress to look anything like the Plain’s Indian dress. They also wanted the dress to be historically correct and if a dress could be found, it had to be documented.
Ms. Stroud flew back to Tulsa and was met by a personal representative of Chief Keeler. It was at that point that Chief Keeler and his handpicked committee of Cherokee women began their search to find a suitable Cherokee outfit for her to wear. Two of the women on the committee were Marie Waddle, a BIA employee, and Wynona Day, the daughter of an influential Cherokee family from the days before statehood. Wynona Day is the person responsible for discovering the dress that became the prototype and model for the modern day Tear Dress. I have recently been told that the dress actually belonged to Wynona Day’s Grandmother or great-grandmother and that it had in truth been stored in a trunk. She had come across it by chance after she inherited her mother's belongings. She remembered having seen the dress and had retrieved it for the committee to examine.

As soon as the committee of women decided that Wynona’s Grandmother’s hand made dress would be perfectly acceptable for the new Miss Indian America to wear as a representative of the Cherokee people, Chief Keeler concurred. The next step was to get a new Tear Dress made for Virginia to wear.
Virginia Stroud’s sister, Elizabeth Walters, who she calls B, made the new dress. She copied the dress line for line, including duplicating the reverse applique on the decorative bands over the shoulders and around the skirt. The dress has a square neckline and no buttons or buttonholes. It closes with hooks and eyes; however the original had no visible means of fastening the dress with modern closures. We believe that according to fashion research, it was common practice for women to use broach pins to fasten blouses and those garments known as waists. Today we would probably just use safety pins. "

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