January Digital Cover Story - Derrick Brownie

Derrick Brownie: Tailoring His Own Path

Derrick Brownie didn’t set out to build a career. He was just trying not to repeat an outfit.

Back in 2015, he started posting photos on Instagram for a simple, almost private reason: he owned a lot of clothes and wanted a way to keep track of what he’d worn. The feed was a personal archive first and a creative outlet second. There was no strategy deck, no monetization plan, no ambition to become an influencer. Just good taste, a camera he wasn’t fully using, and the discipline to show up again the next day.

And then he kept showing up. For years.

Somewhere along the way, brands started paying attention. What began as a side project slowly became something else. For nearly a decade, Brownie balanced a full-time job with a creative practice that quietly grew into a global business, working with brands across cities and continents while still clocking in every day.

Today, Brownie works with clients in New York, Atlanta, and Milan while still calling Indiana home. He suspects that won’t last forever. Not because he wants to leave, but because opportunity still clusters elsewhere. While digital platforms removed the need for permission and middlemen, they didn’t erase the practical reality of needing to be where opportunities concentrate in order to grow.

In many ways, Brownie is representative of the kind of Hoosier Kurt Vonnegut often talked about: regular people from Indiana doing remarkable things all around the globe; talented, creative, hard-working, patient people who carry their sensibilities far beyond the state line.

Now, as then, Indiana continues to produce that kind of talent at an impressive rate. What it struggles with is holding onto it. It’s a familiar story for many emerging and mid-career creatives. Not a desire to go, but a growing awareness that opportunity often asks them to move, taking with it not just talent, but energy, spending power, and the kind of cultural momentum that helps cities grow.

Brownie’s story isn’t really about leaving. It’s about timing. About momentum. About what happens when creatives can build from anywhere, but still feel the gravitational pull of places where decisions, dollars, and density collide. Enjoy! - Polina

Per usual, we’ve edited the transcript for clarity and brevity.

Polina Osherov: You didn’t really set out to build a career on social media. At what point did this start to feel professional to you?

Derrick Brownie: Probably around 2020. That’s when I really started to notice traction. Before that, it honestly just felt like something I was doing for fun. I wasn’t thinking about it as a business at all. It took about five years before it really registered as something more than a hobby.

And I think that’s part of why it worked. I wasn’t waiting for anything to happen. I wasn’t trying to make money or build a career. I just enjoyed documenting what I was wearing. If it had been about money from the beginning, I don’t think I would’ve stuck with it that long.

PO: What were your first major brand relationships?

DB: My first big partnerships were Breitling and Fossil. Breitling reached out in 2019 and asked me to photograph an event at the Reis-Nichols store when they were opening their counter there. Fossil came a little later, in 2020, and that was a six-month partnership where I was creating content consistently.

That was the first time it felt sustained. Like, okay, this isn’t just a one-off thing. This is real work.

PO: What is your dream career trajectory with what you’re doing right now?

DB: My lifelong dream has been to create ads and commercials. Making a Super Bowl commercial is at the top of my bucket list.

But other than that, anything where I can be part of the advertising process, from concept to execution, that’s what I’m really interested in. Being in front of the camera isn’t the goal. I used myself in photos because I didn’t have anyone else, and I knew exactly what image I was going after. But the real passion is creating visuals that make people stop and say, did you see that?

PO: After twelve years in the same job, you finally quit. What tipped the scale?

DB: After ten years, juggling two full-time jobs was no longer sustainable. I was literally burning the candle at both ends; waking up at 7 a.m. for work and editing content until 1 a.m. the next day.

The choice was easy though. I no longer felt fulfilled at my nine to five and the upward trajectory of my side work made the most sense to pursue.

PO: You’ve managed to build an international career while living in Indiana. What has staying here actually made possible for you?

DB: Stability. That’s the biggest thing. Creative work is inconsistent. Some months are great, some months are really bad. Living in Indiana gave me lower expenses and peace of mind. It let me focus on creating instead of constantly worrying about money.

That peace of mind is priceless. It allowed me to invest in camera gear, travel, and take creative risks without feeling like I was one bad month away from disaster.

PO: And where does that start to break down?

DB: Access. There are things that happen in places like New York or LA that you can’t attend day-of. Even though I’m only an hour and a half flight away from New York, there are opportunities I can’t take advantage of because I’m not local. 

Indiana lets me save money and invest in my work, but bigger cities give you more chances to be in the room.

PO: Do you see that as an Indiana problem, or more of an industry reality?

DB: I think it’s structural. Especially for fashion, there just isn’t much of a market here. People move to Indiana to raise families, to go to school, to settle down. Younger people with disposable income tend to move to larger cities.

Until Indiana becomes a place where younger people want to stay and play, it’s hard for industries like fashion to grow at scale. That’s not really a criticism—it’s just how the market works right now.

PO: At what point does staying become a tradeoff rather than an advantage?

DB: When access starts limiting momentum. If a job opportunity came up in New York, or somewhere else, and it made sense financially—if I could find a place there, maybe sublease my apartment here—that would be the tipping point.

It’s really about opportunity density. Indiana works incredibly well as a runway. Bigger markets accelerate things faster.

PO: You’ve started turning down work, which is a shift.

DB: I’m extremely fortunate to be in a place where I don’t have to take on every gig that lands at my doorstep. For example, there was a major brand that’s been around since the 80s and has stores all around the country that reached out for a collaboration. I said no because I didn’t feel I’d be the best representation for their brand. We didn’t align aesthetically.

Sometimes it’s tempting to say yes, but you really have to think about alignment and whether something makes sense for your brand long-term.

PO: What are you saying yes to more of now?

DB: Travel. Especially hotels. A hotel in Indiana feels completely different from a hotel in Miami, and I love interpreting those differences creatively. Now that I’m not tied to a nine to five, I can actually say yes to those opportunities.

PO: What keeps you motivated to keep building?

DB: I’m motivated by things I don’t see enough of anymore. Old movies, for one. I love films that romanticized life. Breakfast at Tiffany’s, To Catch a Thief, Oceans Eleven (2001), to name a few. There was intention there. Everything felt elevated and respected.

I’m also obsessed with Ralph Lauren. Not the clothes, which I’m also a fan of, but the world-building. It’s timeless. It tells a story. It’s not chasing trends, and it doesn’t feel disposable. That kind of work sticks with you.

A lot of what I see today feels very copy-and-paste. Very trend-driven. I’m more interested in originality, even if it’s a little weird. I want to create the kind of work I wish existed.

PO: That feels less like an aesthetic and more like a standard.

DB: Yeah, exactly. It’s not about doing what’s popular in the moment. It’s about making something that still feels good years from now. That’s always been the goal for me.

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This story was made possible thanks to the generous support of our friends at Life in Indy.