SPRINGFIELD – In the summer of 2014, Lenny Underwood said he vividly dreamt that he owned a sock line. When he woke up, he couldn’t shake the feeling that he should pursue this as a business venture. This led to the eventual opening of Upscale Socks, Underwood’s Springfield owned and operated sock business.

Underwood was born and raised in Springfield. He attended Springfield Central High School and went to American International College (AIC) for both his undergraduate and graduate degrees. He earned a Bachelor of Arts in Public Administration with a Minor in Business during his undergrad and a Masters of Public Administration during his graduate level.

While in college, he started a photography business where he photographed campus events. Underwood now works full-time in photography and shoots weddings, headshots and more.

After dreaming about owning his own sock line, Underwood said he told his friend about it and began toying with the idea of making it a reality.

“I just really believed that something out of that dream could happen,” he said. “We thought it was a cool idea, but he and I had never worked in retail before and knew nothing about the process of getting started.”

Underwood said that for a year after the initial dream he did research on starting the business. He wanted to figure out how much it would cost and began reaching out to business owners and entrepreneurs for guidance. However, he said that he didn’t receive many responses.

“I kept hitting those walls, but I just kept going,” he said.  

Underwood then pursued a seven-week startup business program called Spark Holyoke, now known as EforAll, which he said was key in the development of Upscale Socks.

In the summer of 2016, Underwood hired a graphic designer to help him with designs, a business name, a tagline and more. In December 2016, Upscale Socks was officially launched.

Upscale Socks is now sold online and in several businesses in the area. The socks can be found at the Visitor’s Center in Springfield, Bumpys Natural & Organic Foods in Springfield, Out of The Box Gift Shop in Ludlow as well as ROAM in the Berkshires. Underwood said he hopes the socks will soon expand into other stores as well.

“We’re working on some more, hopefully by the end of the spring we will be sharing on social media where they can also be found, but the primary location is online,” he said.

Upscale Socks sells both children and adult socks with different designs. Children's socks begin at $5.99 and adult socks begin at $11.99. Underwood said that many styles have a story to them and are Springfield, New England and Massachusetts inspired. He said he encourages people to buy his socks because they are made locally, designed locally and help give back to the community.

“If you’re from the area you can certainly want to be a part of something that is Springfield-based and locally made, owned and operated,” he said. “We give back to the community, so you’re part of something that’s bigger than just purchasing a pair of socks. You’re also impacting those that may be in need.”

During the 2020 holiday season, Upscale Socks partnered with Educare Springfield and, for every pair of socks purchased, donated a pair back to the children of Educare. Underwood said that 333 pairs of socks were donated.

Upscale Socks also created a design to raise funds for Breast Cancer Awareness last year.

In the coming months, Underwood said that Upscale Socks will be working on a Mother’s Day and Father’s Day campaign and will also partner with the Mental Health Association to design a pair of socks supporting Mental Health Awareness Month in May.

Underwood said that he is excited for the future of his business and to see what new opportunities and partnerships arise.

“I’m excited about more partnerships with organizations, meeting people I don’t know and supplying people for their wedding, maybe even photoshoots, certainly excited about expanding to other parts of the country,” he said. “I’m enjoying the slow and steady pace that I’m on and seeing the potential for it to even blow my mind and reach places I’ve never even heard of.”

Those interested in learning more or purchasing Upscale Socks are encouraged to visit their website at https://www.upscalesocks.com/.