Mary Phelps Jacob was born into a wealthy and socially prominent New York family. This privileged background provided her with access to education and cultural opportunities that would later shape her independent spirit and artistic pursuits. Her upbringing, however, also instilled in her a sense of the restrictive nature of societal norms for women, something she would later actively rebel against.

While preparing for a debutante ball, the young Mary Phelps Jacob found her whalebone corset cumbersome and unflattering under her sheer gown. Frustrated, she devised a solution using two handkerchiefs, ribbon, and cord – creating what became known as the 'backless brassiere'. Her innovation quickly gained popularity among her friends, offering a liberating alternative to the constricting corsets of the era. This ingenious invention would later be patented.

Recognizing the commercial potential of her invention, Mary Phelps Jacob obtained a patent for the 'backless brassiere.' Although she initially sold the patent to the Warner Brothers Corset Company for a mere $1,500, the invention paved the way for the modern bra and represented a significant step toward female liberation from restrictive undergarments. Ironically, the bra would later become a multi-billion dollar industry.

Mary Phelps Jacob married Harry Crosby, a charismatic but troubled Harvard graduate and World War I veteran. This union marked a turning point in her life, leading her away from the conventional social circles of her upbringing and towards a more bohemian and avant-garde lifestyle. The marriage was passionate but turbulent, marked by Harry's erratic behavior and increasingly dark obsessions.

Caresse and Harry Crosby established the Black Sun Press in Paris, a publishing house dedicated to printing experimental and often controversial works by emerging and established writers. The press became a significant force in the literary world, publishing early works by authors such as James Joyce, Ernest Hemingway, D.H. Lawrence, and Ezra Pound. Caresse played a pivotal role in the press's success, acting as editor, translator, and business manager.

Caresse and Harry Crosby became central figures in the Lost Generation of expatriate writers and artists living in Paris during the 1920s and 1930s. Their lavish parties and salons attracted a diverse group of intellectuals and creatives, fostering a vibrant atmosphere of artistic experimentation and intellectual exchange. Caresse's wealth and social connections enabled her to support these artists financially and promote their work.

Harry Crosby's life ended tragically with a suicide pact in New York City. His death deeply impacted Caresse, forcing her to confront her husband's demons and the challenges of continuing the Black Sun Press without him. Despite the immense grief, Caresse persevered, demonstrating her resilience and commitment to the literary world.

After her husband's death, Caresse returned to the United States and founded Hampton Manor, an artists' colony in Virginia. This utopian community provided a haven for writers, artists, and musicians, offering them a space to live, work, and collaborate. Hampton Manor reflected Caresse's ongoing commitment to supporting the arts and fostering creativity.

Caresse eventually returned to Europe, continuing to engage with the art world and pursue her own creative endeavors. She remained a patron of the arts, supporting emerging talents and organizing exhibitions. She moved to Italy and continued her own writing, focusing on poetry and memoirs.

Caresse Crosby died in Rome, Italy, at the age of 77. Her life was a testament to her independent spirit, her unwavering support of the arts, and her willingness to challenge societal norms. She left behind a legacy as a literary patron, publisher, and an early pioneer of female liberation.