While enjoying an afternoon at Katy Trail Ice House, a Dallas beer garden, 26-year-old Palmer Dean uncovered a gap in the t-shirt market. Looking around he saw people who looked like visitors, wearing undistinguished mainstream brands with distracting logos. Being native to Dallas, Palmer felt he should do something to bring back hometown pride and show Dallas in a simple yet fashionable light. Thus, OutlineTheSky was born.


Founder and CEO, Palmer Dean

We sat down with Palmer for a Q&A session to find out more about the company that has sold over 2,000 t-shirts in less than six months, and – of course – chat about the logo they picked to represent their booming business.

– What makes OutlineTheSky unique? OutlineTheSky is unique in two ways. Firstly, we are creating skyline designs no one has ever done before. Having a simple one-line format to create the skyline and the capability to customize it to any city gives us an amazing edge. Secondly, we offer quality material. Why buy apparel that will take you 30 to 40 washes to get it to that perfect feel when we can offer that right off the bat?

– Did you learn anything about branding, or your vision for your company, while running your design contest? The feedback aspect of the site is what helped me convey to the designers what I needed. Through much discussion, we were able to land the perfect design and logo for OutlineTheSky. I found that branding is a simple concept yet tricky to launch. We are still finding our way but have started carving out our own brand. It is so exciting!

I knew I needed something that wasn’t too specific, as it would corner us into being “oh they just do that.” Our name, OutlineTheSky, leaves some mystery but doesn’t limit us. I needed to encompass all this in a logo and our winning designer executed it perfectly.


Design by gelaptakgulita; check out OutlineTheSky’s logo design contest here

– How do you think your new logo has impacted your business? We have seen tremendous growth in the first six months due to the combination of our name and logo. It’s great in its simplicity, and while it looks like a city skyline (which has propelled our business thus far), it’s adaptable to any industry. We get great feedback and people are loving it.

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The logo is all over everything we do: proposals, tagless labels in our clothing, social media, pricing sheets, PowerPoint presentations, business cards and even my personal devices. I don’t do anything without our logo attached.

– How have you been able to reach new customers? I believe social media is the greatest marketing tool for a startup. We have seen more sales through responses to contests, giveaways, discount codes and celebrity postings than any advertising placement thus far.

Our Instagram and Facebook base is growing at a rate of about 100 followers per month, which directly affects our website sales. We are also able to co-brand with companies such as Kendra Scott, St Bernard Sports, The City of Dallas Convention & Visitors Bureau, CultureMap, and others. It’s great to get their customers engaged with what we are doing and get our customers engaged with what they are doing.

– One of your aims was to bring back local flavor to fashion. How have Dallas natives responded to your initiatives? The feedback has been tremendous. We’ve had numerous social media comments, press coverage and retail partnerships. More cities are partnering with us because of our brand now. Even this past weekend at the State Fair of Texas we met a customer, a University of Texas student, wearing an Outline shirt – we took a photo with him!


Palmer Dean and co-founder Rex Womble meet a customer at the Texas State Fair

– You started this company with a great idea and an iPad – any advice for fellow budding entrepreneurs? I think people sometimes prevent themselves from reaching their goals or dreams by psyching themselves out. Don’t ask a lot of questions but just do it. Either way you will end up on a road of growth and learning. No one else will be able to define your success or failure but yourself. My entire goal was to sell just one shirt. If I could do that, I would have proven successful.

Palmer and his team have sold over 2,000 shirts (and counting!). Besides Dallas, they now print skylines of Austin, NYC, and LA – and a year from now they’re anticipating to have designs for 30 cities around the globe. We at 99designs have already put in our order for the San Francisco and Melbourne skylines, but in the meantime: let’s all represent a little bit of Texas.