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Cross Dressing as a Means of Escaping Enslavement

18th Century Examples of Cross Dressing and Gender Role Reversal by Freedom Seekers

August 1776 escaped slave notice for Maria, who disguised herself in men's clothing to escape enslavement in New Jersey.

IN MENS CLOTHES.
RUN away the 30th of July last, from the Jerseys to Philadelphia or New-York, a MULATTOE Woman Slave named Maria; had on a white or red and white jacket, white ticken breeches, white stockings, old mens shoes, and an old beaver hat; she is hardly discernable from a white woman, is rather thinish visage, middle size, thick legs, long black hair, and about 35 years old; she hath left behind her three young children, a good master and mistress, and is going towards New-York after a married white man, who is a soldier in the Continental service there. Whoever secures the said Mulattoe in goal, and will immediately advertise the same in this paper, shall have FOUR DOLLARS reward.
The Pennsylvania Gazette, 14 August 1776.


Introduction

Little more than a month had passed from the adoption in Philadelphia by the Second Continental Congress of the unanimous Declaration of the thirteen united States of America, formally separating itself from Great Britain, to the more surreptitious declaration of freedom by a young woman in New Jersey who escaped from her enslavers. The first declaration was immediately published in Pennsylvania newspapers and read publicly in New Jersey and Pennsylvania. These bold moves by prominent men of the thirteen colonies subjected them to arrest and imprisonment for high treason, and as a result their actions and words are enshrined in history textbooks throughout the world. The actions of Maria, a young African American woman, were no less bold and would also subject her to capture and imprisonment, but would be unknown had her enslaver not published a detailed escape notice in the Philadelphia newspaper The Pennsylvania Gazette.

Like many people held in bondage, Maria found her situation intolerable and she acted on it by committing a crime: she "stole" herself away from her enslavers, an unnamed family in New Jersey. Colonial America was dependent upon involuntary forced labor for its survival. Indentured servants, imported European servants, convicts, paupers, orphans, indiginous people, apprentices and slaves all labored under typically harsh conditions. Those in the best situations were adequately fed and clothed and the most fortunate were taught a trade over many long years. The great majority of these persons, however, received substandard food, cast-off clothing and poor lodgings in exchange for long hours at hard labor. None of them were free.

Many people in bondage simply left, taking to the road at night and causing their masters and mistresses to publish escape notices, such as the one above for Maria. These escape notices filled the pages of colonial American newspapers. Sometimes a dozen or more ads appeared in a single four-page edition. The notice placed by Maria's enslaver stands out from others, however, due to the attention-grabbing headline "In Mens Clothes."

A Bold and Shrewdly Chosen Disguise

Most escape notices found in colonial and early republic newspapers included information about the clothing worn or taken by the escapee. Aside from a physical description, spotting someone in clothing that matched what was printed in an escape ad was the most useful means of identifying that person as a runaway. Escapees and freedom seekers knew this and often changed their clothing at the first opportunity in order to evade detection.

Maria's decision to dress in the clothing of a working man was a bold and shrewd move. Shrewd in that the "white or red and white jacket, white ticken breeches, white stockings, old mens shoes, and an old beaver hat" were all common types of summer apparel that any working man might wear and would not stand out. Bold because she had to do more than just wear the clothing of a man. In order to pull off her disguise, she had to successfully present herself as man, which meant her looks, physical build, hair, mannerisms, walk and voice must not arouse suspicion. The ad describes her physical characteristics as "rather thinish visage, middle size, thick legs, long black hair," all of which could work in her favor. She had one more very important physical characteristic contributing to a disguise: her enslaver noted she was "hardly discernable from a white woman." A white working man traveling alone would arouse fewer suspicions than a lone Black man and far fewer than a lone Black woman.

An Earlier Example

October 1742 ad for three escaped servants from Maryland, including an African American woman dressed in men's clothes.

RUN away from the Subscriber, living at Elk-Ridge in Anne-Arundel Country, Maryland, the 26th of September, 1742, the following Servants, viz. John Simms, a Convict Servant Man, well set, about 30 Years of Ages, and is of a pale Complexion; he is without his Hair, and had on when he went away, a Castor Hat, a ruffled Holland Shirt, a Flower'd Vest, a Pair of new Pumps, and blue ribb'd Stockings. Also, Thomas Handfield, a Convict Servant; he is a young raw Youth, about 18 or 20 Years of Age, fresh coloured and somewhat pitted with the small Pox, wears his own yellow curl'd Hair, had on a Castor Hat with a Gold Button and Loop, his other Cloaths unknown.
Likewise, a Negro Woman named Jenny, supposed to be dressed in Man's Cloaths; if so, she has on a Felt Hat, an Oznabriggs Jacket, a Pair of check'd Trowsers, and an old Pair of Mens Pumps. If she is in Woman's Apparel, she has on a Country Cloth Habit, a Hempen Roll Petticoat, she is a slim young Wench, looks smooth, with large Eyes. Whoever apprehends the said Servants and brings them to the Subscriber shall have Ten Pounds Reward for the Three; or Three Pounds each for the Men, besides what the law allwos, and Four Pounds Reward for the Woman.
John Howard
The Pennsylvania Gazette, 28 October 1742.

Jenny escaped along with two white convicts from John Howard in Elk Ridge, Maryland, in late September 1742. Howard's escape notice gives details about each of the escapees, noting that Jenny was "supposed to be dressed in Man's Cloaths." Like Maria, Jenny chose working men's clothing. As a "slim young Wench," she could probably pass for an older teenaged boy or a very young man. Howard's notice also lists specific items of woman's apparel that she might be wearing, making it likely she took the woman's clothing along with her.

Clever Disguise, or Challenging Gender Roles?

In choosing to escape enslavement as men, were Maria and Jenny simply attempting a clever disguise, or were they actively rebelling against gender roles? Not enough is known about either woman to conclude their cross dressing was anything more than a means to aid their escape. The wording of the escape notices, however, provides subtle clues that leave open the possibility that both women were comfortable in clothes of the opposite sex. Jenny, in 1742, was "supposed" to be dressed as a man. The word "suppose," as used here, implies a strong belief -- something more than a guess. Why would John Howard assume such a bold disguise?

In addition, Howard described the exact styles, patterns and fabric of the men's garments that Jenny wore when she escaped. Servants and enslaved people were typically clothed as cheaply as possible, usually in cast-off, turned and mended second-hand clothing. Only rarely were any provided with more clothing than was absolutely necessary. That Howard could provide a detailed description of every item of clothing worn by each of the three escapees shows that he was intimately knowledgable about their everyday clothing. Is it possible that Jenny wore the described men's clothing to perform daily chores on Howard's plantation?

Maria's enslaver was so sure that she wore men's clothing during her escape that it was announced in a headline. As with the advertisement for Jenny, the exact style, color and fabric of Maria's garments were described. Further, her enslaver stated that her reason for leaving was to meet up with a soldier in the Continental Army, then encamped in New York state. Both British and American armies had large numbers of civilian women accompanying troops for various reasons. They provided valuable and necessary services, from cooking, laundry, and companionship, to carrying baggage and nursing the wounded. But these women remained in traditional female clothing, even to the point of having to continually wash and mend the single dress or gown they wore. A regimental or army jacket might supplement a very worn and faded dress.

What, then, did Maria intend to do when she caught up with the troops dressed as a man? If she had taken women's garments along with her in her escape, her enslaver would have mentioned it in the published notice. All clothing, even that worn daily by slaves, was property of their enslavers. When an enslaved person escaped, they were not only "stealing themselves," they were stealing the very clothing, hat and shoes they wore. Did Maria intend to "join up" and fight as a man? There are instances of women fighting in American units disguised as men. Deborah Sampson, who fought for seventeen months with the 4th Massachusetts Continental regiment, is a notable example. But if Maria was pursuing a specific man in the regiment, it is doubtful that was her intent as she would be quickly found out.

Margaret Grant Dresses as a Boy Servant

1770 escaped slave notice of Margaret Grant who escaped by dressing as a boy servant to a white indentured convict man.

Thirteen Pounds Reward.
RUN away, on Saturday the 10th instant, from the subscribers, living in Baltimore town, Maryland, the following servants, viz, JOHN CHAMBERS, an English convict servant man, about 21 years of age, 5 feet 7 or 8 inches high, of a pale complexion, gray eyes, and bandy legs; had on and took with him sundry suits of clothes, nine ruffled shirts, a brown bush wig, a pair of single channel boots, a blue cloth great coat, and 150 £ cash, which he robbed his masters house of on the night of his elopement.

MARGARET GRANT, a mulatto, about 20 years of age, 5 feet 1 or 2 inches high; had on and took with her sundry womens apparel, but has since disguised herself in a full suit of mens blue clothes, attending as waiting boy on the above John Chambers. She is an artful hussy, can read and write, has been in Barbados, Antigua, the Grenades, Philadelphia, and says she was born in Carolina. Whoever apprehends the said servants, and secures them and the money, so that their masters may have them again, shall have the above reward, and reasonable charges, if brought home, paid by
HENRY JAMES.
MORDECAI GIST.
March 14, 1770.
N.B. All masters of vessels are forbid to carry them off, at their peril.
The Virginia Gazette, 22 March, 05 April 1770.

Richard Wood, also known as Polly Wood

1779 ad for Maryland escaped slaved Richard Wood.

TWENTY DOLLARS REWARD.
RAN AWAY about two months ago, from the subscriber, living near Chester Town, Kent County, Maryland, a Negro Man named DICK, about five feet eight or nine inches high, of a yellow complexion, round shouldered, and remarkably stout and bony. I have some reason to believe he is either in Wilmington or Philadelphia, as he was met on that road making up the country. He is a very artful fellow, and generally goes by the name of Richard Wood, but frequently dresses himself in womens cloaths and then calls himself Polly Wood, and the deception is not easily detected as he can cook, spin, knit, wash and iron as well as most women. He affects to have fits, which I do not believe to be real. Whoever will secure the said Negro in any gaol, so that I may have him again, shall receive the above reward, or if brought home, reasonable charges, paid by
DEAN CANNADAY.
January 24.
Dunlap and Claypoole's American Daily Advertiser, 18 February 1779.

The two escape notice above, from 1770 and 1779 illustrate two very cunning gender role reversals. Margaret Grant escaped from Mordecai Gist in Baltimore by donning "full suit of mens blue clothes" to pose as a servant to escaped white convict John Chambers. Margaret was a well educated woman, being able to read and write, and had experienced enslavement in three different countries in the Caribbean, as well as in Philadelphia and her place of birth in the Carolinas. As a result of this world-wise experience, albeit while enslaved, she had apparently developed the ability to negotiate and survive in a variety of cultures and situations. Her enslaver, Gist, desparaging referred to her as an "artful hussy," and in discounting her intelligence, was unable to hold on to her.

While Margaret Grant's adoption of a male personna seems to have been purely to effect an escape, Richard Wood, who escaped from Dean Cannaday in Chestertown, Maryland, had a more complex situation. Although he escaped in men's clothing, Cannaday noted that Richard Wood "frequently dresses himself in womens cloaths and then calls himself Polly Wood." While Cannaday implies this may have been a way for Wood to evade capture after the escape, his remarks that Wood was a "frequent" cross-dresser and also skilled at chores commonly associated with females indicates Wood might even have identified as trans-gender. Wood, according to Cannaday, performed those chores "as well as most women." With the little information available in the escape notice, however, Wood's activity may have been no more than a desire to be viewed as a woman from time to time.

Concluding Remarks

The enslaved persons above all defied gender and sexual role boundaries for various reasons. Whether their intent was purely to effect a clever disguise to avoid capture or to actively challenge gender roles is known only to them. Regardless of intent, their activity would have been unknown except for their even more bold move in refusing to accept enslavement and taking charge of their own freedom and destiny.

 

Notes

At some point, Mordecai Gist recovered Margaret Grant and promptly sold her to another enslaver. By April of 1773 she was enslaved by George Ashman, Jr. in a nearby part of Baltimore County, from whom she escaped on April 21st of that year:

1773 escaped slave notice of Margaret Grant, who escaped from George Ashman in Baltimore County.

April 24, 1773.
RAN away the 21st of this instant from the Subscriber, living near Gunpowder meetinghouse, in Baltimore county, a mulatto woman named Margaret Grant, about twenty years old; she is very short and well set, and appears to be big with child, can read and write, is a good needle woman and cook, and can wash and iron very well; she says she was born in Charles-town, in South-Carolina, and has been in Philadelphia and the island of Grenada; had on, when she went away, a white holland jacket, new gray half-thick upper petticoat, and white country kersey under ditto, much worn, with holes in it, osnabrig shift, lawn cap, a white linen handkerchief, or a blue spotted ditto, with holes therein, much worn high heeled leather shoes, with white metal buckles.
Whoever takes up the said woman, and secures her, so that her master may get her again, shall receive three pounds reward, if taken more than ten miles from home, and reasonable charges if brought home, paid by
GEORGE ASHMAN, junr.
N.B. The aforesaid woman about three years ago was a servant of Mr. Mordecai Gist, in Baltimore town, and is well acquainted there. All masters of vessels are hereby forwarned against carrying her off.
Additional research has not found any evidence that George Ashman ever recovered Margaret Grant.

The advertisement for Jenny, who escaped along with two convict men in September 1742 from John Howard in Maryland, was published through November 25, 1742.

There were no statutes in colonial Pennsylvania prohibiting cross-dressing. It was not, however, considered acceptable behavior and was regarded with extreme suspicion. In the summer of 1752 a white woman named Charlotte Hamilton, who had been travelling the region for years in men's clothing peddling elixers door-to-door as Dr. Charles Hamilton, was imprisoned in Chester County. The cause of her imprisonment, though, was not for cross-dressing, but because the local authorities suspected her of fraud and were holding her temporarily in the event that anyone came forward to accuse her of cheating them. Details of her capture are below:

PHILADELPHIA, July 16.
Extract of a Letter from Chester, in Pennsylvania, July 13, 1752.
"On Thursday last a Person, that went by the Name of Charles Hamilton, came here, and offered to Sale at several Houses in Town sundry Medicines for different Disorders; pretending he was brought up to the Business of Doctor and Surgeon, under one Doctor Green, a noted Mountebank in England; and that he embarked on board a Brigantine, at Topsham, in England, last Fall, for Philadelphia, one Robinson Commander, but was cast away the latter end of January, on the Coast of North-Carolina; and that he had travelled from thence through Virginia and Maryland, and has a Pass signed by some Magistrates in Virginia and Maryland, and one in Newcastle County: But it being suspected that the Doctor was a Woman in Mens Cloaths, was taken up, examined, and found to be a Woman; and confessed she had used that Disguise for several Years. She is very bold, and can give no good Account of herself; says she is about Twenty-eight Years of Age, tho' she seems to be about 'Forty. She wears a blue Camblet Coat, with Silver Twist Buttons, too large for her. She is detained in Prison here, till we see whether any Body appears against her, if not, she will be discharged. She says now her Name is Charlotte Hamilton." (The Pennsylvania Gazette, 16 July 1752.)

Finally, the some people in post-Revolution Pennsylvania expressed fears that society had entered a period of moral decline. The following essay appeared in Philadelphia's The Independent Gazetteer, in response to a young woman spotted on the streets of the city in men's breeches. It aptly sums up the social disapproval of cross-dressing that had prevailed up through the Revolution, but was now increasingly being challenged by a younger generation that had come of age during the Revoluton:

For ther INDEPENDENT GAZETTEER.
Aimed at somebody.
"Some men to business, some to pleasure take,
"But every woman is at heart a rake."
POPE.

Mr. OSWALD,
THE express commands we frequently meet with in sacred writings, to submit with patience and resignation to those afflictions human nature is liable to, should arm us with becoming fortitude, to banish from our thoughts dire despair, instead of encouraging audacious customs which only afford us a melancholy reproach.
I have been led into these reflections from the horrid and too frequent perpetration of youth ruining their reputations. A friend of mine says, had the girl (whom he met on the street last week) dressed in man's cloaths, reflected but for one moment when she put on the breeches, which never was intended by nature for her or any of her female associates-- had she but reflected (says he) but one moment, she must have viewed herself with horror, and consequently have quitted the wicked purpose of her heart. As the laws of this country are ineffectual to prohibit this audacious sin, let a mark of infamy be stamped upoen the memory of the person, who thus publicly exposes herself to the embrace of every libertine; and let them always be remembered as long as they live, living in their sins; and when dying-- dying like a hadrened resolute hussy unworthy of the name of woman.
I have read an author who describes a country where if a woman deviated from the laws, they publicly appeared for three successive Sundays in the midst of the congregation in the church where she belonged, and the man in black cloaths lessoned her and told her the evil of her doings. Shame, delicacy and modesty had a stronger effect upon the amiable sex, than the most cruel punishment that could be inflicted upon them. Let us, therefore, Mr. Editor, renew the golden age, and not drown our senses and reason in sensuality, intoxication and gay company; let us apply in our distress to that merciful and tremendous Being, who is always ready to grant us his gracious assistance, and able to extricate us out of all our troubles and afflictions.
I wish some abler pen than mine might be employed in searching out the cause which induces girls, who go under the appellation of modesty and virtue, to use such desperate effects, at the manifest hazard of ruining themselves to all intents and purposes.
The humble station providence has allotted me, has not prevented me from observing, that this daring infringement on the laws of modesty and nature, is generally perpetrated by persons of a sullen phlegmatic temper, whose haughty appearance render them very unsociable associates to those who are qualified to make good members of society. If these uncultivated animals were to embrace the opportunity, and view (in a proper light) those audacious scenes of misery which they glory in exhibiting, "I am persuaded, says a correspondent, their consciences would reprove them." -- "And" continues he, "if their eyes were opened, it would induce them to live contented till that little god (fly Cupid) was pleased to send them an agreeable bed-fellow, which (says he) is the daily prayer of every girl aftern fifteen."
LARGO.
Philadelphia, February 8, 1787. (The Independent Gazetteer, 09 February 1787.)

Sources

  • The Pennsylvania Gazette, 14 August 1776.
  • The Pennsylvania Gazette, 28 October, 25 November 1742.
  • The Virginia Gazette, 22 March, 05 April 1770.
  • Dunlap and Claypoole's American Daily Advertiser, 18 February 1779.
  • The Maryland Gazette, 13 May 1773.
  • The Pennsylvania Gazette, 16 July 1752.
  • The Independent Gazetteer, 09 February 1787.


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