Evangelista later moved to New York City and signed with Elite Model Management. She then moved to Paris to further her career. She worked extensively with fashion photographer Peter Lindbergh who encouraged her to consider a short do. Top hairdresser Julien Dy's then cut her hair into what she described as "a bowl cut with sideburns". She cried during the haircut but it turned out to be the defining moment of her career.
Evangelista once uttered the quote, "We don't wake up for less than $10,000 a day", (often misquoted as: "We don't get out of bed for less than..." or "I don't get out of bed for less than...") Spoken in Vogue (1990) to Jonathan van Meter, talking about money and how she and a few other models were calling the shots and changing the game.
In 2007, she signed a multiple-year exclusive contract with the cosmetics company L'Oreal Paris. It was announced in early 2008 that she would be featured in the Prada Fall 2008 campaign seen in magazines internationally.
She is signed to DNA Model Management in New York City, and Models 1 in London.
In June 2010, the New York Post reported that Evangelista will be the new face of
At the age of 22, Evangelista married Elite executive Gerald Marie. They were married from 1987 to 1993. After separating from Marie, she began a 6-year relationship with actor Kyle MacLachlan, and then divorced Marie.
In 1999, she became pregnant by French football player, Fabien Barthez. At 6 months pregnant, she delivered a stillborn baby. The couple then broke up and Evangelista left modelling for several years to recuperate.
On October 11, 2006, Evangelista gave birth to a boy, Augustin James, refusing to name his biological father, which sparked numerous rumours. While pregnant, she appeared on the August 2006 issue of Vogue. In late June 2011, Evangelista filed court papers that revealed her son was fathered by billionaire Frenchman François-Henri Pinault, by then the husband of actress Salma Hayek. After several court appearances aimed at establishing a child support agreement, on August 1, 2011, Evangelista formally filed for a child support order in Manhattan Family Court, seeking $46,000 in monthly child support from Pinault. It was reported that if granted, this amount "would probably be the largest support order in the history of the family court".A heavily-publicized child support trial began on May 3, 2012,and included testimony from both Pinault and Evangelista with Evangelista's attorney claiming that Pinault had never supported the child. Several days into the trial, on May 7, 2012, Evangelista and Pinault reached an out-of-court settlement.