For a long time, Middleton was the only Black woman in the room, oftentimes the only Black queer person in the room. She worked in corporate America as a designer. Her work appeared in several prominent sports businesses including ESPN and The Undefeated. She was successful in her field, rising through the ranks to a creative director position.
Then, 2020 happened. George Floyd and Breonna Taylor were tragically murdered. And Middleton experienced racial prejudice herself. She, along with her family, were kicked out of a restaurant in Florida. The events of that year, for Middleton, stopped everything.
“I felt like I was just cruising through life, thinking that I had worked hard to be successful when I still wasn't really free,” she said. “I was just in this box. So once I got out the box, I wasn’t free. Once I wasn't at work, I’m still a Black person. And there are still places I can’t go, especially being openly queer. It's still like, I’m walking down the street and people look at me funny. So we’re free, but are we really free?”
2020 affected Middleton deeply and gave her a desire to do more. She wanted to provide some type of change to the world. Living through those experiences made her consider what’s important in her life, which was her family and her people.
“It was like, no matter how hard I work, no matter how much I had to rise up in the ranks at my job, it wasn't going to make a difference between my life,” she said. “It was a life and death thing to me.”
She sought to create more opportunities for her family and people like her. And through her background she realized something was missing. She understood how underrepresented Black culture was. Even when her designs included Black men or Black athletes, most of the time they catered toward a commercialized, white audience.
Middleton noticed especially there was a need for more products designed for Black women. She loved to wear sports apparel, but found there weren’t as many streetwear options for Black women to wear.
“I felt like we were very marginalized group,” she said. “A lot of times people disrespect Black women or look down on us or don't give us credit.”
Throughout her life, Black women surrounded Middleton and shaped her into the person she is today. They saw her at her best and at her worst. Her mother is the most important person in her life. She looked up to public Black figures such as Queen Latifah, Beyonce, Lil Kim and Nicki Minaj.
“Being around a lot of Black women, that move a certain way, that can handle business on and off the court, it’s just a different vibe” she said. “It gives you a different grit. It's kind of like this connectedness, far and wide.”
So, Middleton didn’t wait. She worked to promote more Black voices. Middleton built her own brand called Trenches which focuses on creating streetwear and community for the Black queer creatives in the local community. The clothing line includes messages to protect Black women and celebrate Juneteenth.