Caresse Crosby designed the first modern bra using two pocket handkerchiefs, ribbons, a needle, and thread. She pinned the handkerchiefs together on the bias as a friend sewed the ribbons to the points below Crosby's breastbone. Crosby then knotted the handkerchiefs' ends around her waist while her friend pulled the ribbons taut and attached them to the knots at Crosby's waist. Besides providing comfortable support, Crosby's brassiere flattened full bosoms as much as possible, which conformed to the style of the time--the virginal appearance. The simplicity of her bra was appealing because it lacked buttons, bones, and hooks that pressed painfully into women's flesh, thus marking and causing the skin to redden and swell. Other young women were impressed by her ingenuity and asked Crosby to construct similar garments for them. Wearing comfortable clothing and undergarments was important to this group of young women, as their main social outlet was attending balls. Some sources credit Crosby's invention to the year 1913 (instead of 1914), but this may be due to her faulty sense of chronology.

The popularity of Crosby's invention surpassed her immediate social circle. After Crosby received a letter from a stranger asking to buy her brassiere for a dollar, she turned her eye toward the possibilities of entrepreneurship and took steps to protect her idea. A Harvard law clerk, Mr. Jones, employed by Mitchell Chadwick & Kent, assisted Crosby's patent application for a corselette, essentially a corset cover that served as an undergarment but which lacked whalebone support and construction. Jones's excitement about the product was evidenced by a series of schematic brassiere drawings that he produced for her the next day. Originally, Jones asked Crosby for $50 to file the patent, but she could not afford the fee. They agreed that she would pay $5 up front and an additional sum once the patent was obtained. Jones filed the application on February 12, 1914.

Crosby borrowed $100 from a friend and rented a room in the sweatshop district of Boston. She rented two sewing machines and employed two Italian girls to sew brassieres according to her design. They produced several hundred backless brassieres, which Crosby took great care in packaging and marketing. She made personal calls to three department stores that each bought one dozen bras. Unfortunately, the bras did not sell. Crosby failed to pursue additional marketing opportunities because she was occupied by her wedding plans. She sold her patent years later for $1,500, a large sum at that time, through Johnny Field, a contact she had at the Warner Brothers Corset Companyin Bridgeport, Connecticut.

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