‘I Don’t Let Fear and Doubt Win’

One presentation—sprinkled with Jay-Z lyrics—may have been the difference between practicing law and a career in design for Dionna Dorsey.

‘I made a presentation for my Dad, and I explained that even though I wouldn’t make as much in the beginning as a designer, if he supported me now, one day I’d return on his investment. Next thing I know, I’m living in Milan.’

It may have been the most important pivot in her life, but Dionna began carving out her own path long before then.

Born in Springfield, Va., Dionna spent weekdays with her mom, a flight attendant based in Pittsburgh. On most weekends, summers and holidays, she flew to DC to live with her Dad on Capitol Hill—frequently enjoying Sundays along the Georgetown waterfront. Early on, she realized she was living in two different worlds.

‘I always sensed a ceiling in Pittsburgh, even if I didn’t know what it was at the time. I just knew I had more access to do different types of things in DC.’

Growing up, Dionna was told she’d do a great many things, but designing and owning a clothing line were never part of the picture. Still, she couldn’t shake the calling.

‘I was told I was going to go to law school, I was going to be a lawyer, and I could be the first female Black president. But there’s a moment I can see so clearly in my mind. I had a lot of hair as a young child and it would take my mom hours to do it. She would lay me on one side to do half my head, then the other. One day, while doing my hair, we were watching a grey movie and I saw this beautiful woman cascading down the steps. I shot up and said, ‘Mom, who is that?!’ It was Audrey Hepburn. She would become my first muse.’

Fifteen years later, Dionna eventually conceded to law school—with every intention of eventually selling her father’s law firm and building a fashion house. But when she opened her first LSAT book, Dionna knew immediately she couldn’t go through with it.

After undergrad, she started her first clothing line, Dionna Marie—traveling back and forth to Milan and nearby towns with empty suitcases to carry fabric. The dream was taking hold.

‘Biella was No. 1 in the world for wool at the time and my college boyfriend lived there. I would walk around and share my story, in my broken Italian, that I was a penniless graduate who wanted to start a clothing line and I desperately needed good fabric. Somehow it worked, and quite amazingly too.’

One afternoon, she got lost in Milan and wandered into Istituto Marangoni, a fashion design school near the Duomo. Dionna grabbed a brochure, and pitched her parents on enrolling once she returned home. A few months later, she moved to Milan to study fashion design.

‘I don’t think I’ve ever thought I was brave, but when I look back at that young lady, I’m like wow, girl—and I’m really proud of her. You don’t appreciate these things until you have a little perspective.’

Now the founder of Dionna Dorsey Design and District of Clothing, Dionna says her evolution has been full of failures since those early days in Italy. She just doesn’t let the fear and doubt win.

‘I fail fast, fail forward, and I cling to my faith. And I’ve learned that often times, the fear and the doubt you feel comes from sharing your ideas with others. It’s not necessarily your fear or doubt; it’s theirs being cast onto you. I’m always incredibly nervous, but I just don’t let it stop me. I pivot instead. Progression requires many things and one of them is the ability to pivot.’

Most recently, Dionna has pivoted back to Georgetown. With a focus on equity, equality, and community in everything she does, she began working with the Georgetown BID to foster conversation around those topics.

‘I had an office space here for two years and had gotten some flack from working and contributing to businesses here, because Georgetown has the perception of not being inclusive. But Georgetown is such a staple community and it was incredibly diverse a very long time ago. I believe in community and unity for all people, and if I’m doing work in areas or communities that don’t have all of the access and resources of Georgetown, I believe I also have to be doing the work in Georgetown. There has to be a coming together from both perspectives.’

That morphed into Gather Georgetown—a community dinner and discussion she co-hosted last Fall with the Georgetown BID for nearly 20 diverse DC entrepreneurs and business owners—all of whom openly shared their unique perceptions of the neighborhood. She hopes it’s the first of many such dinners that will help bridge a gap that has grown in the community.

‘I’m very much a believer in building. It may take some time to change perceptions, but you can’t look at a challenge and think of how big it is. You have to look at an idea and consider how to build it out so it will solve the challenge. I love my country, I love this city, and I believe I have a unique ability to do some work that can potentially open up some doors and hopefully change a few minds. I hope Gather is a part of that conversation and action.’

Both a ‘dreamer and a doer,’ Dionna credits much of her success to constantly moving—regardless of the direction. Now, she’s building more time for reflection.

‘The older I get, the more I pause to get to better know me. I’m meeting myself again at a really interesting time.’