Intimate Apparel takes place in 1905 and follows Esther Mills, an African American seamstress, who makes lingerie for the wealthy women uptown and the ladies of the night downtown.  When the owner of Esther’s boarding house, Mrs. Dickson, gives her a letter from a mysterious man in Panama, Esther’s world begins to shift.

George, one of the many Afro-Caribbean men building the Panama Canal, asks if he may write to Esther. Knowing Mrs. Dickson does not approve, Esther, who cannot read nor write, shows the letter to Mrs. Van Buren, one of her wealthy, white clients. Mrs. Van Buren helps Esther answer George’s letter, and their long-distance romance is born.

Esther also tells her friend Mayme, an African American singer, piano player, and sex worker, about George’s letters. Mayme, who can read and write, helps Esther describe her physical attributes to George, something Esther could never ask Mrs. Van Buren to do. Mayme and Esther dream about the future together, and Esther reveals that she has been saving the money she makes sewing to open a beauty salon for African American women to feel pampered. All of her money is sewn into a colorful quilt that Esther keeps on her bed.

Esther buys her fabrics from Mr. Marks, a Romanian Orthodox Jewish immigrant. Esther and Mr. Marks have a clear attraction to one another, yet, of course, their racial and religious differences prevent them from pursuing any romantic involvement. Mr. Marks’ religion prevents him from even touching Esther. But it does not prevent their enjoying the fabric together.

After months of writing back and forth, George writes that he will come to America and asks Esther to marry him. Esther broaches the subject with all of the people in her life—Mrs. Van Buren, Mayme, Mrs. Dickson, and Mr. Marks—in various ways. At the end of act one, Mr. Marks gifts Esther a gorgeous fabric for her wedding gown, and George and Esther are married. A camera flashes, and the super title appears, “Unidentified Negro Couple ca. 1905”.

Act two picks up on George and Esther’s wedding night. It is the first time we see them speak to each other in person. George is a little rougher than Esther imagined him to be, and he scoffs at the beautiful smoking jacket she made for him (out of fabric Mr. Marks saved just for Esther).

Further problems for George and Esther arise when George cannot get work in construction as he planned. Esther has been opening up her quilt to give George money, and it is clear that he spends it drinking and gambling at night. He is frustrated at the race relations in America and feels infantilized by having to take money from his wife.

Throughout all of this Esther continues to work and see Mrs. Van Buren, Mr. Marks, and Mayme. Mrs. Van Buren mistakes Esther’s veiled talk of her affection for Mr. Marks as affection for Mrs. Van Buren herself. Mrs. Van Burn kisses Esther, and it ruins their relationship.

Mayme has found a man herself, however the man is married, and, for the first time, Esther considers the wives at home waiting for their husbands who are out with the women Esther sews for. Then Mayme shows Esther the beautiful smoking jacket her new man gave her—it is the one Esther made for George. Esther says nothing to Mayme of her knowledge of the identity of Mayme’s lover.

At home, George asks Esther for all of the money in her quilt to buy a team of horses from a man he sees at the bars. Esther is hesitant. She confronts George about his letters, and he reveals he paid someone else to write them; he too can neither read nor write. George paints a beautiful picture for Esther of the life they will lead once he has these horses. He will be the picture perfect husband, and she the happy wife. Esther gives him the money. He leaves, even though Esther begs him to stay.

Esther goes to Mayme who wants Esther to leave because her new man is coming. Esther tells Mayme her new man is George. When he comes to Mayme’s door, she doesn’t answer.

Esther takes the smoking jacket to Mr. Marks. He is touched by the gift, and it is the closest they ever come to speaking truth to their love for one another.

Esther then returns to the boarding house and Mrs. Dickson takes her back, no questions asked. Esther ends the play sitting at her old sewing machine, touching her belly (perhaps indicating she is pregnant?). Camera flash, “Unidentified Negro Seamstress ca. 1905”.