[3] Originally a long-haired redhead,[4] she reinvented her look in the early 1990s by having her hair cut short and dyed black,[5] and her eyebrows shaved off.
McMenamy attended Notre Dame High School in Easton, where she reportedly received excellent grades[13] but was often teased by her classmates, who called her "Skeleton" due to her lanky body.
[16][19] McMenamy's modeling career mainly spanned the years 1985 to 1998, when she worked for several of the world's top designers and international fashion houses, including Versace, Giorgio Armani, Valentino, Todd Oldham, Christian Dior, Sonia Rykiel, Dolce & Gabbana, Jean Paul Gaultier, Gianfranco Ferré, Lanvin, Isaac Mizrahi, Yohji Yamamoto, Thierry Mugler, Comme des Garçons, Chloé, and Moschino.
[citation needed] During the beginning of her modeling career, McMenamy met photographer Peter Lindbergh, with whom she worked extensively, and Chanel head designer Karl Lagerfeld, who helped mentor her.
In 1986, she was featured in the book A Day in the Life of America, photographed by Sante D'Orazio,[21] and also appeared in advertisements for Gerard Darel and Alberta Ferretti.
She worked with several fashion photographers, including Albert Watson, Helmut Newton, Richard Avedon, Steven Meisel, Ellen von Unwerth, Arthur Elgort, Paolo Roversi, Patrick Demarchelier, Jean-Baptiste Mondino, Tim Walker, David Sims, Max Vadukul, and Juergen Teller.
"[23] Some of the other magazines that she has been featured in are Harper's Bazaar, Vanity Fair, People, Interview, Elle, V, Dazed & Confused, LOVE, i-D, The Face, W, Women's Wear Daily, and Newsweek.
[14] In 1992, after having her long red hair cut short and dyed black, makeup artist François Nars shaved off her eyebrows for Anna Sui's fall/winter fashion show, thereby "ushering in the era of grunge".
[29][32] In October 1992, she opened the Versace spring/summer 1993 womenswear fashion show, and she later appeared in the ad campaign for that collection, photographed by Avedon.
[17][18][34] The following month, she had six red ribbons painted on her back, for an amfAR benefit event that she co-hosted with Leanza Cornett.
In 2006, she appeared on the cover of the book In Vogue: The Illustrated History of the World's Most Famous Fashion Magazine along with Evangelista, photographed by Meisel.
In the September 2009 issue of Harper's Bazaar, she wore no makeup for a feature story titled "Supermodels Supernatural".
[46][51] A few days later, she closed the Louis Vuitton spring/summer 2011 fashion show wearing body paint that was intended to look like zebra stripes.
[66] In July 2022, while closing the Gaultier fall/winter 2022 haute couture fashion show wearing a bridal gown, McMenamy tripped on her high heels and fell on the catwalk, with several audience members rushing to her aid.
[72] Several people reportedly "criticised the Italian luxury fashion house for showcasing shoes that appeared too difficult to walk in",[73] which prompted McMenamy to post on her Instagram page that she did not fall because of her heels or the outfit, but blamed herself for the mishap.
[74] In September 2023, McMenamy was a guest celebrity judge in the episode Stitch & Strut of the British reality television series RuPaul's Drag Race UK broadcast on BBC Three.
[75] In the early 1990s, McMenamy became romantically involved with Hubert Boukobza, the owner of the Paris nightclub Les Bains-Douches.
[30][76] The relationship came to an end, and later, McMenamy began dating English fashion photographer Miles Aldridge, whom she met on a photoshoot for W magazine.
Her wedding dress was designed by Karl Lagerfeld, who gave her away,[78][79] and she wore a headdress made by the milliner Philip Treacy.