Ad Age is marking Black History Month 2023 with our third-annual Honoring Creative Excellence package. (Read the introduction here.) Today, the actor, singer, director, producer, composer and playwright Billy Porter—our first guest editor of the month—serves up the backstory on his most legendary fashion moment. (Visit our package hub each weekday for a new essay from another notable Black creative.)

My Aunt Dorothy used to always say, “Dress for the job you want. Not the one you have!”

I decided early on in my “Kinky Boots” journey that I was going to serve geek-chic-realness for all press events associated with my return to Broadway, after a decade hiatus. We were playing Chicago for our out-of-town tryout, and I came out of the stage door after our first preview and greeted some kind patrons. I even took pictures and signed autographs. I woke up the next morning to those photos scattered all over the internet. OMG! The internet did not exist the last time I trod the boards. I look like a bag lady!

I immediately started showin’ up and showin’ out! Every single day was more geek-chic than the next. Colored and patterned blazers. Collared shirts with bow ties and pocket squares. I continued this tradition for my three-year run as Lola in “Kinky Boots.” My colleagues were confused. My business manager insisted I stop spending so much of my money on clothes.

Then in the fall of 2013, after winning the Tony Award for Best Actor in a Musical, and the Grammy for Best Musical Theater Album, I won a holiday campaign for The Gap, posing with the legendary Cyndi Lauper (who was herself a Tony Award-winner for Best Score for “Kinky Boots”). I felt slightly vindicated. 

Fast-forward to 2019 and I am nominated for a Golden Globe for my work on the groundbreaking FX series “Pose.” After attending several Hollywood events that week, I woke up on the morning of the awards to a headline in The New York Times that read: “Golden Globes 2019: At the Parties, the Winner Is Billy Porter.” I did not win the award that night, but I felt a shift happening. My champagne, custom-couture Randi Rahm suit—with a silk cape embroidered with spring flowers and a fuchsia lining—did not disappoint!

The invitation to host the red carpet at the Oscars came out of nowhere. And the first thing I did was panic. What am I going to wear? I had watched my friend Idina Menzel become a household name when John Travolta botched her name at the 2014 Oscars, calling her “Adele Dazeem” when introducing her performance of “Let it Go” from Disney’s “Frozen.” I knew this was my Adele Dazeem moment and was not gonna throw away my shot! 

I was attending my very first New York Fashion Week, and while sitting front row at the Christian Siriano show I was so moved by the organic diversity and inclusion that embraced us all. Models of all shapes, sizes, colors, creeds, sexualities and binaries were well represented. I used to always joke back when I was in drama school that I was gonna break binary norms and wear a gown to the Oscars. I thought I was joking, but words—even the unconscious ones—have power. Turns out I had already spoken and manifested this moment in my life decades prior. 

I cornered Christian on the dance floor at his after-party and pitched him my idea: traditional tuxedo on top, antebellum ball gown on the bottom. And the rest is history. I had no idea that this one little act of simply being my pure unadulterated, authentic self would reverberate all over the world and blow up the gender norms in fashion forever.

I’m humbled. I’m honored. And … you’re welcome!