She advocated going to cosmetology school part-time while finishing her high school degree to her principal and started learning at the Gene Juarez Beauty Academy, which she calls "the nicest salon in Seattle," in their advanced training centre.
"You would pay to be in this program, but you would also work and get paid," Cunningham said. "I did the laundry, I swept, and I got people coffee. It was the best job, and I was so inspired." She did that while nannying for Bette Midler, who paid for the schooling.
It wasn't all smooth sailing. Being self-taught, a lot of what Cunningham was learning in beauty school went against how she had always done it. "I remember one of my teachers telling me that I didn't hold my blow-dryer properly — I don't hold it where everybody else holds it, I hold it by the nozzle," said Cunningham. "She said, 'You're not doing it right,' and I looked at her and said, 'If you can blow-dry hair as good as me, then I'll hold my blow-dryer like you.' That was not good to say."
After beauty school, Middler introduced her to Lily Aldridge's parents, Laura Lyons and Alan Aldridge, and her older brother Miles Aldridge, a fashion photographer (Lily was only four at the time). Miles had recently shot a W Magazine cover, which happened to be for former stylist Art Luna, or "Hollywood's Hippest Hairdresser," as the cover said in bold letters. Cunningham knew instantly that she had to work there and reached out. "It was a great experience," she said.
After that, word of her work spread in the celebrity circle. She began working with Portia de Rossi, then came Anjelica Huston, Angela Featherstone, and Renée Zellweger. It was all through word of mouth. "I thought I was sort of the flavour of the month, but it kept going," said Cunningham.