Literally Outside is the brainchild of Steffan Williams, a Cedar Rapids native who found himself searching for more outside time (literally) after he moved to Chicago. In 2021, he founded the company as a clothing brand with purpose. Read on to hear the story of his small business and where he hopes to take it in the future.

Born During a Pandemic
I grew up in Cedar Rapids, Iowa, and basically grew up outside. I have really strong core memories of going on long hikes as a family but once I got into the “real world,” that all kind of disappeared: I basically took a 30-year hiatus from hiking and connecting with nature.
Then the pandemic happened. The world shut down and my family and I were trapped inside most of the time. So we started taking post-dinner hikes with the kids. We took a few trips centered around hiking. We went to Sedona, Arizona and Asheville, North Carolina. I fell back in love with hiking, being outside, and being connected to nature.
Even as I rediscovered that spark, I noticed that there weren’t many people of color out on the trails. I realized I wanted to share this love of the outdoors with others who may, like me, have lost it when they got to adulthood or who may not feel comfortable entering this space.
Plus, I’m a huge clothing and apparel person; I collect Jordans and Nikes and all that. I’m also really into “gorpcore,” which is a fashion trend that blends outdoor functionality with everyday urban style (“gorp” stands for “good ol’ raisins and peanuts,” a classic hiking trail mix). Founding Literally Outside let me join my two worlds: this rediscovered love of the outdoors and my lifelong interest in fashion.

Creating a Brand that Evolves
When we started Literally Outside, we created an initial wordmark that was very minimalistic. We needed a simple brand that would allow us to evolve, an emblem that could work on different shapes like a circle patch. Those worked really well to launch the brand, but as we went on we discovered that not everyone in our audience wanted that minimalist look. So we’ve been evolving, tracking what people like and engage with on social media, and paying attention to our sales.
We do a lot of in-person pop-ups which let us see people’s reactions right away. I’ve found that people tend to like the stuff that gets a little more crazy, a little more Y2K and metallic. That’s been a really fun evolution for the brand.
Lately, we’ve been working with different artists to create pieces for us that follow the trends our customers are after. Sometimes for those we use different L/O logos. We’re not married to our original branding and feel a lot of flexibility while staying true to our foundations. I know that’s not the case for every business, but it works for us.

The Value of Collaboration
I love finding artists to work with on Instagram. I’m a firm believer in just asking for what you want. I’ll DM people and let them know: “I saw your portfolio, I love what you’re doing, and this is what I’m trying to do with my brand.”
The last few artists we’ve worked with have come strictly from reaching out on Instagram and now I consider them friends, which is really cool. It benefits the artists, too, because when we collaborate with someone, we introduce them and their art to our followers.
Authenticity Over Photoshoots
As much as Instagram has helped us, it’s also been a big challenge because the algorithm is always changing. But, I’ve found that being authentic to our voice and our goals—instead of posting just to post—is key. We try to post less frequently, but with intent, so that when people do see us in their feeds, it’s with a specific goal: to turn over sales, or to get new followers, or join an event or do something social like that. It’s just trial and error and you really have to put yourself out there.
We’ve had some really great feedback when we actually don’t post about our products and instead post about a running event, or a climbing event, or something that actually connects people in the real world. Those authentic posts have served us better than something polished from a photo shoot.
What’s Next
We’ve been lucky to get noticed by some bigger brands; right now we’re featured in the REI store in Lincoln Park in Chicago. It’s really cool to stop by and see our pieces for sale there.
I’m really excited about our first cut-and-sew program, meaning that we’re designing our own custom pieces. For our other pieces, we’ve applied our branding and style to existing blanks from a manufacturer. But I found a designer in the UK who’s great; she focuses on outdoor lifestyle pieces. She actually reached out to me on Instagram and expressed interest in working with us! Right now, we’re designing a bag, a hat, and other pieces.

What I Need Most
A million dollars! Just kidding. (But not really.) My main focus is always to get our name out there because I would love the ability to cast a wider net. We have quality pieces, we work with really cool artists, and the name of the brand itself genuinely speaks to people. I was at an outdoor merchandise festival in Colorado recently, and we sold over 80 units in a day. People kept telling me how much they loved our name, which was great but it means that they’d never heard of us before! So that’s always something I’m working on.
The Takeaway
All in all, I’m so glad I started Literally Outside. Previously, I was working in cyber security sales. I enjoyed that but it was stressful knowing that if you didn’t make your numbers you were on the chopping block. Now, I’m motivated by my own goals and by my audience to succeed. I’ve met amazing people, I feel that what I’m doing is rewarding and impactful, and my kids see me doing something that makes me happy. That’s valuable and worthwhile.
Thanks, Steffan, for taking the time to chat with us about your journey to founding and growing Literally Outside. If you’re a growing business and you’re looking for marketing expertise, get in touch!