We caught up with the brilliant and insightful Darryl Glover a few weeks ago and have shared our conversation below.

Darryl, appreciate you joining us today. Do you wish you had started sooner?

I had a wierd “day in August” 3 years in a row. The first year… I realized it was time to make a change, The second year, I realized I wasn’t ready to survive on my own with out consistent – weekly income….(yet) and the third year I jumped. literally. I turned in my resignation, finished out my contract, and jumped out of a plane the next day. It was time for a new beginning…I was 25

I would have started sooner. had I been exposed to costume design as a career in grade school. I began my career in fashion in 2011 at age 25. Friends of mine were telling me to join this new app called Instagram. I’d just resigned from my position as a teacher in Newark, NJ and I was ready to put all the NY Fashion week dressing, editorial pitching, and fashion styling and costume design certificate courses from FIT to the test, The 2 years of teaching till 3PM then running the streets of Manhatten until 10 was over and it was all on me.

I was so excited and eager to make the transition into the world of fashion. I had no clue my lack of exposure would affect me down the line. Simply put. I wish I started sooner. Now I firmilly belive that we are all called according to the gifts we carry, and we all have our own unique journey, however, there are certain skills that can only be cultivated through experience.

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers.

I’ve always been drawn to storytelling—whether through fashion, film, or the transformative power of education. My journey into the creative industry has been anything but traditional, but every step has shaped the work I do today.

I started in fashion as a stylist and costume designer, initially balancing my time between teaching in Newark, NJ, and running through the streets of Manhattan, working backstage at NY Fashion Week, pitching editorial concepts, and earning a certification in costume design from FIT. Eventually, I took the leap and committed to fashion full-time, styling for major productions and working with clients in the entertainment industry. But as I gained experience, I also saw a major gap—access. Too many young creatives, especially those from underprivileged communities, weren’t being exposed to careers in fashion, entertainment, and the arts.

That realization led me to found That Day In August, a nonprofit designed to expose the arts as a career option to inner city students. Through in-person and digital programming, we introduce students to creative careers they might never have considered, connecting them with professionals who can mentor and guide them. Our Careers in Arts Education Expo travels nationwide, offering hands-on experiences that demystify creative industries and make them feel attainable.

What sets my work apart—both in fashion and through my nonprofit—is the deep belief that creativity isn’t just about aesthetics; it’s about access, representation, and opportunity. Whether I’m styling for a project or developing arts programming, I’m always thinking about impact. I want my work to inspire, to open doors, and to challenge the idea that success in the creative industry is only for a select few.

I’m most proud of the moments when my work changes someone’s trajectory—whether it’s a young person seeing themselves in a creative career for the first time or a client feeling transformed by a look I’ve styled for them. At the end of the day, I want people to know that my work—whether in fashion or education—is about more than just the surface. It’s about telling stories, creating opportunities, and inspiring the next generation of creatives.

Can you tell us about a time you’ve had to pivot?

I feel like I’m in the middle of a pivot season right now. While I’ve spent years building a career I love as a fashion stylist and costume designer—crafting visual stories for clients in entertainment and media—I’ve felt a deeper call growing louder: a call to lean further into storytelling in its broadest, most impactful form.

This next chapter is about more than clothes—it’s about legacy, access, and community. As I continue to grow my styling and design company, I’m also pouring energy into building That Day In August, a nonprofit that lives at the intersection of creative expression and youth empowerment. We’re designing programming that opens doors for students who may have never imagined themselves working behind the scenes in fashion, film, or the arts.

One of our newest initiatives is the 15/15 Podcast, where we’ll spotlight 15-minute conversations with creative professionals who share both their journeys and the real behind-the-scenes of breaking into the industry. It’s about visibility, mentorship, and showing students that there are many ways to show up creatively in the world.

My current pivot season also includes expanding my entrepreneurial responsibilities—moving from being the CEO of one company to now overseeing multiple ventures, from That Day In August to other creative and business endeavors that reflect my evolving purpose and vision.

This pivot isn’t about leaving styling behind—it’s about expanding the story. I want people to know that behind the polished looks and cinematic costumes, there’s a purpose. That Day In August is my way of making sure the next generation sees themselves reflected in the industries that shape culture—and knows there’s space for them to thrive.

This is the beginning of something bigger, and I’m so excited to finally share it.

What’s the most rewarding aspect of being a creative in your experience?

Some of the most rewarding aspects of being an artist and creative are the opportunities to contribute to shape-shifting moments that move culture forward. Whether it’s through a look that captures a movement, a costume that deepens a character’s story, or a program that opens a young person’s eyes to their own creative potential—I get to be part of moments that mean something.

There’s a certain freedom in this work—the freedom to create without limits, to imagine worlds that don’t yet exist, and to tell stories that might otherwise go unheard. That freedom is sacred. It allows me to not only express myself but to reflect the world around me in ways that challenge, heal, inspire, and empower.

Being a creative means having the power to shift perspectives, to spark conversations, and to influence how people see themselves and others. That’s not something I take lightly. Every project, every design, every workshop or podcast episode is an opportunity to leave a mark—one rooted in intention, culture, and community.

Contact Info:

• Website: www.godarrylgo,com
• Instagram: @godarrylgo
• Linkedin: https://www.linkedin.com/in/godarrylgo

Image Credits

Antonio Jefferson Studios