Cannon grew up in New York City and was influenced at an early age by rock and fashion. He is an award-winning celebrity stylist, fashion editor and creative director who has styled many of his favourite celebrities, from Cyndi Lauper to Shirley Manson.

His wit, charisma and style has made him a trusted and sought-after stylist by Hollywood legends such as Liza Minnelli and Glenn Close. Cannon has also worked with some of today's hottest celebrities, including Elizabeth Banks, Sam Rockwell, Angelina Jolie, Matt Damon, and Penn Badgley. He was the first stylist to get Barbara Walters into a pair of jeans for a photo shoot, and had the opportunity to dress Michael Jackson as the King of Pop for MTV.

As a result of working with great musicians and celebrities, Cannon has contributed to multiple publications including Rolling Stone, Vogue, Time, Entertainment Weekly, Vanity Fair and W. He has styled large casts for every network including This is Us, Mr. Robot, Homeland, Mrs. America, The Sopranos, Project Runway, The Today Show, and The Office.

Cannon's expertise in fashion also has lent itself to his being in front of the camera as a style expert, with television appearances on E!, VH1, NBC, ABC, TLC, and Bravo. Cannon has been an on-air spokesperson for brands such as Pantene, TJ Maxx, Burlington, Dove and Peanuts/Snoopy Worldwide.

Additional commercial work also includes Sony, Amazon, Saks Fifth Avenue, Target, Sony Music, Bergdorf Goodman, and Neiman Marcus. Cannon has styled fashion shows for Jason Wu and the Life Ball in Vienna, Austria, which is the largest AIDS benefit runway show in the world, that year hosted by President Bill Clinton and Eva Longoria.