The Round 2 Interview
Round Two by Round Two is the spinoff brand of popular hype and vintage store Round 2. They have grown in popularity alongside the store since its inception in 2013, first as shop merch and now as a successful brand. We spoke to the Sales and Marketing Coordinator Alex Vanecek (@luciusleftfoot) regarding the future of Round Two, the influence of vintage on their design process and the role Sean Wotherspoon plays for the brand.
YMM: What is your name and role at Round Two?
A: My name is Alex Vanecek and I’m the Sales and Marketing Coordinator at Round Two Designs LLC.
YMM: What’s the story behind Round Two Chicago and why did Round Two choose Chicago as the location for their fifth store?
A: Chicago has always had a rich sneaker history so it seemed like a good fit for Round Two. Our first location had a giant Michael Jordan Shrine on the wall so it was a cool full circle moment for us. The city has been great, we hope to do some events or pop-ups in CH-I next year.
YMM: How has The Show on YouTube helped Round Two grow both as a store ad as a clothing brand?
A: The Show was massive to the growth of the brand. We really gave a free blueprint on how to open your own buy/sell/trade store. Our filmer Graham started a family so things have slowed down on Youtube, BUT we are working towards getting monthly episodes back in the mix. It will be a big help for the brand.
YMM: How did Round 2 develop from a merch brand to its own clothing line?
A: Growing the brand seemed like the next logical step for Round Two. The buy/sell/trade business has changed drastically over the last 5 years so in terms of growth, the brand made the most sense.
YMM: What does the team at Round Two by Round Two look like?
A: The team is pretty small, it’s basically me and one other guy, Haile Cano. He’s our Photographer and Ecommerce Coordinator. Sean Wotherspoon and the other owners chip in with design concepts and ideas. But most of the work is handled by myself and Haile. We work in a big office that houses other brands as well called “Lightwork”. They have their own internal staff that help us with CADS and certain production things, which is huge. I’ve worked retail my whole life so getting this behind the scenes look at the clothing industry has been fun. Very eye opening.
YMM: How involved is Sean Wotherspoon with Round Two and its designs?
A: Sean is a big part of the brand. He brings a lot of ideas and inspiration to the table, then we get to work on bringing the ideas to life. A lot of our designs come directly from vintage pieces. We have an extensive archive that we can pull from and bring things to the modern age. We’ve referenced pieces as far back as the 1950s, and all the way to the early 2000s.
YMM: What’s the design process for each new Round Two collection like?
A: The design process usually starts with finding a reference piece. Whether that’s a pre-existing article of clothing, an album or book cover, even old advertisements bring a ton of ideas to the table. We then bring our design and production teams into the mix and get their help with choosing materials and locking down the fit.
YMM: What are some of the biggest inspirations behind Round Two?
A: Our single biggest source of inspiration is vintage clothing. We love finding something from 30-100 years ago that doesn’t exist in today’s market, and showcasing it to the modern consumer. We love examining different styles and cuts throughout history.
YMM: Between WHR, C’est Bon, and Compton Cowboys, Round Two seems to love collaborations, what collabs are up next for the brand?
A: At this point collabs are a must for any brand, clothing or not. That being said, I think licensing and collaborations are becoming less and less genuine, and the consumer can see through it 9 times out of 10. We are hoping to showcase smaller brands that we love like WHR and C’est Bon, while also securing collaborations with big brands that helped inspire Round Two to become what it is today. We have some big things on the way!
YMM: Explain the WHR collab and how that came to be.
A: The WHR collaboration came very organically. They sent Sean a hat with their patented bungee strap and he loved it! We reached out, they were down to work together, and the rest is history. We held an event at our Vintage Store and had a great time with them. Shoutout Punker Pat!

YMM: Dream collab?
A: So I will speak just for myself with this one, I would love to do a sneaker collaboration of some sort. I think a Round Two Reebok Club C could be really cool, that’s a timeless silhouette and I’d love to take a crack at it.
YMM: What does the future look like for Round Two?
A: The future looks super bright for the Round Two brand. We have a big collab releasing at ComplexCon this November that I think will really surprise people. The collections for 2023 are our best yet, we can’t wait to share them with the world! We are also hoping to branch out into more retailers next year. We have a few international shops that carry the brand currently, but we are hoping to boost that number a lot over the next 2 years.
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