[6] Cleveland's career as a model began in 1966 when she was on a subway platform with a friend en route to class and was noticed by the assistant to Carrie Donovan, fashion editor at Vogue.
Donovan, impressed by Cleveland's fashionable clothing, invited her to tour the Vogue offices and the magazine subsequently published a feature on her as an up-and-coming young designer.
[7] Following her tour with Ebony, in which she experienced acts of violent racism in the Southern United States,[3] Cleveland caught the attention of designers such as Jacques Tiffeau and Stephen Burrows.
[7] Soon she was meeting and working with many of the fashion industry's top enterprising people of the era, including Diana Vreeland and being photographed by Irving Penn, Steven Meisel, Richard Avedon, Christopher Makos, and Andy Warhol[8][9] and briefly became a muse to Salvador Dalí.
[2] She relocated to Paris at the suggestion of fashion illustrator Antonio Lopez in 1971, and soon became a house model for Karl Lagerfeld, who was the main designer at Chloé.
[3] During the 1970s, Cleveland modeled for designers such as Valentino, Oscar de la Renta, Yves Saint Laurent, Thierry Mugler, Diane von Furstenberg, and Christian Dior.
With Karen Bjornson, Anjelica Huston, Alva Chinn, Elsa Peretti, and Pat Ast, among others, she became one of Halston's favored troupe of models, nicknamed the Halstonettes.
The gala, which pitted five French designers: Yves Saint Laurent, Hubert de Givenchy, Pierre Cardin, Emanuel Ungaro and Christian Dior's Marc Bohan, against five American designers: Bill Blass, Oscar de la Renta, Anne Klein, Halston and Stephen Burrows in a fashion showdown.
The event became an international fashion extravaganza with style writers and society columnists, wealthy socialites, royalty, tycoons and politicians in attendance.
[14] The gala later was chronicled in the 2015 Pulitzer Prize winning The Battle of Versailles: The Night American Fashion Stumbled into the Spotlight and Made History by Robin Givhan.
From the early to late 1970s, she appeared on the cover of Vanity Fair, Interview, Essence, Harper's, Cosmopolitan, Women’s Wear Daily, L'Officiel, The Sunday Times Magazine, GQ,[3] Vogue Paris, W, and Elle.
[21] In 2014, she walked the runway for Moschino's Spring Collection in Milan and appeared on the cover of Numéro Russia, shot and styled by Tom Ford.
Donations were made from many individuals within the fashion industry, including designers; Anna Sui, Kim Jones, Marc Jacobs, Zac Posen, Thierry Mugler, Kimora Lee Simmons, and Elsa Peretti; models Carla Bruni, Helena Christensen, Marisa Berenson, Marpessa Hennink, and Lineisy Montero; photographers Inez van Lamsweerde, Vinoodh Matadin, Roxanne Lowit and Steven Klein; stylist and fashion journalist Katie Grand; and businesswoman and DJ Marjorie Gubelmann.