Upscale Socks Makes Dreams a Reality

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Founding Father Benjamin Franklin once said, “I never leave home without a nice pair of socks.”

That’s the philosophy behind Upscale Socks, a Springfield, Massachusetts-based designer sock company founded by Leonard Underwood. For Underwood, a nice pair of socks can change your whole outfit, and even, your mood.  

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“For men who work in corporate America, accessories like socks can jazz up their outfit in a subtle way without being over the top,” Underwood says. “A pair of socks with bold colors can get someone’s attention. They’re a conversation piece.”

Underwood wears many hats: photographer, personal trainer, business owner. The idea for his latest endeavor came to him in a dream, literally. One night, the entrepreneur dreamed he owned a sock business. When we woke, he set out to make that dream a reality.

“It started off with a dream in 2014. I feel like there’s purpose behind that,” Underwood says. “I’d never worked in retail before. I didn’t know how to get started. No one really wanted to help and give insight. But I really believed it was meant to be.”

A pair of socks with bold colors can get someone’s attention. They’re a conversation piece.
— Lenny Underwood
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Before Underwood launched Upscale Socks in 2016, he’d never worked in retail. However, what he lacked in knowledge, he made up for in entrepreneurial spirit.

“I’ve been an entrepreneur all of my adult life,” says Underwood. “I take pride in making my customers satisfied. It’s not about instant gratification and seeing things happen overnight, but gradually seeing things progress, to build something and leave a legacy.”

Today, Upscale Socks offers 70 styles and has plans to expand its children's line this year. From whimsical designs, to sharp, standout patterns for professionals, the retailer offers something for everyone with adult and kid sizes. Prices range from $5.99 for a pair of children socks, to $14.99 for a pair of adult socks.

 “Our socks make you feel good and more confident. Our socks are comfortable. They give you great support. We offer matching styles for the whole family so you can match with your kids as well,” Underwood says. “I’m really pleased with the trajectory we’re on.”

 Now that Underwood has made his dream a reality, he strives to help others do the same. Upscale Socks funded a scholarship for a local high school senior to attend college. The company also hosted a sock-designing contest where they welcomed submissions from local schools. The winner of that contest had their design added to Upscale Sock’s selection.

The retailer has also donated more than 1,000 pairs of socks to local community organizations and nonprofits as part of their “Suit Your Soles” campaign, where they match a sock donation for every purchase.

“It’s important to us to partner with the community,” Underwood says. “Knowing the community has always been there for me even when I didn’t realize it, I want to make sure I do my part to suit their souls. That’s our tagline. By giving back in a small way, I feel like I’m doing my part in  making a difference and affecting change.”

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This profile has been designed as part of the brand awareness campaign for Upscale Socks, created by the team at Stand Out Truck®.  

Stand Out Truck® is great at storytelling and brand awareness campaigns via our roaming digital billboard trucks. Contact us today to promote your business.

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