Kelly started his career as a freelance writer for several fashion magazines and was an editor for Marie Claire and Mademoiselle.

When your style is aligned with who you are, you feel empowered.”[7] Kelly is openly gay, but in comparing What Not to Wear with the show Queer Eye—which pioneered gay men making over people seen as needing fashion advice—the Washington Blade noted some key differences: "[U]nless you have your gaydar on while watching the show, you would have no idea.

“It wasn’t just about the clothes; I felt I could continue empowering through this.”[10] Kelly became the moderator of the ABC daytime show The Chew in 2011.

Kelly was selected for The Chew after meeting a producer who had read his 2008 book, “Freakin’ Fabulous: How to Dress, Speak, Behave, Eat, Drink, Entertain, Decorate, and Generally Be Better Than Everyone Else.”[11] He did several screen tests, where the chemistry with his co-stars were evident, and started the show in 2011.

[12] The show was more reflective of Kelly’s interests and actual life, when not on TV, as it covered food, entertaining, and lifestyle topics.

In 2015, Kelly shared the Daytime Emmy Award for Outstanding Informative Talk Show Host with his cohosts on The Chew.

The show featured one-hour episodes where 10 bakers compete for the ultimate grand prize of $25,000 and the title of Champion.

Kelly described the experience of writing his memoirs: This book really was about finally allowing myself to open up to the people who watched me on television for the past 15 or so years.

In 2008, Kelly wrote Freakin' Fabulous: How to Dress, Speak, Behave, Eat, Drink, Entertain, Decorate, and Generally be Better than Everyone Else.

[21] In 2005, Kelly and Stacy London co-wrote a book titled Dress Your Best: The Complete Guide to Finding the Style That's Right for Your Body.

[22] He has also created a popular web series on his social media called Basic Grammar for Basic B*****s. The web series is a light-hearted approach to educating people on common grammar mistakes, examples are often taken from trolls who have posted on his social media.

“I wanted something different, something fun.” He approached the space with “no rules” and endeavored to mix color, texture, pattern, and shine to reflect his personality.