Cutrone was born and raised in Camillus, New York. She graduated from Syracuse University with a degree in Nursing.
She moved to New York at age 21 and began her career in public relations after being introduced to Susan Blond, a prominent New York publicist, by her writer/socialite acquaintance Anthony Haden-Guest, who had suggested that she become a publicist. Cutrone became Blond's assistant for a year and went on to become director of PR at Spin magazine for Bob Guccione. Less than a year later, Cutrone launched Cutrone & Weinberg with former Susan Blond intern, Jason Weinberg. The duo represented Eartha Kitt, CC Music Factory, Nile Rogers, Frank Sinatra, Cafe Tabac, Hollywood Palladium, The Roxy, The Limelight, Dee Lite, The William Morris Agency and many more. Cutrone has been married twice. At 21, she married Andy Warhol's protégé, artist Ronnie Cutrone, and at 28 married actor Jeff Kober. Both marriages ended in a divorce. She has a daughter with Italian Ilario Calvo, named Ava Cutrone in 2002).
In 1991, Cutrone sold her half of the Cutrone & Weinberg and moved across the country to Los Angeles, California. She studied Eastern Mysticism, Meditation and Tantra - became a tarot card reader and soon signed a record deal with Atlantic Records in Los Angeles. Her album was produced by music industry legend Richard Perry. Cutrone founded People's Revolution in 1996. The company has grown into one of the most powerful fashion PR companies in the world, representing and producing shows for such brands as Longchamp, Vivienne Westwood, Valentino, Jeremy Scott, Paco Rabanne, Thierry Mugler, Bulgari, Christie's, Agent Provocateur, Costello Tgaliapietra, KTZ, Francesca Liberatore and more in London, Paris, Moscow, Los Angeles, New York and Milan.
On September 11, 2002, People's Revolution broke the record for the most shows produced on one day during New York Fashion Week—five—mainly because they were the only company willing to produce shows on the first anniversary of the September 11 terrorist attacks.
Cutrone has said that she named her company People's Revolution "not because I'm a communist—a popular misconception—but because I happen to believe the world will change only when we change ourselves."
Cutrone is known for her no-nonsense approach to the fashion industry. She has appeared on three MTV: True Life, The Hills—on which she employed Whitney Port and Lauren Conrad—and The City, where she served as the professional/personal mentor and employer of Port and consulted on Port's clothing line.
In February 2010, Cutrone executive produced Bravos's Kell on Earth, the eight-episode series was a reality show about Cutrone and People's Revolution and followed Cutrone as she balanced running her own company and producing Fashion Weeks in New York and London with being a single mother.
In February 2010, HarperOne, an imprint of HarperCollins, released Cutrone's memoir, If You Have to Cry, Go Outside: And Other Things Your Mother Never Told You. The book is co-authored by Meredith Bryan, and is a New York Times bestseller. Cutrone's second book, Normal Gets You Nowhere, was published May 3, 2011.
In November 2010, she signed on as a contributor to the Dr. Phil Show. In 2011 Cutrone replaced Vogue Editor André Leon Talley as a judge America's Next Top Model for seasons 18, 19, 20, 21, 22.
Ms. Cutrone appeared in Terrence Malick's "Knight of Cups" March 2016.
Cutrone has spoken at two TEDx event: the first at University of Oxford's independent TED event, TEDxOxford, in which she gave an inspirational 18-minute talk about her career, and the second at TEDxAmsterdamWomen, during which she spoke about her journey as a woman in business.