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Daily News

SPRINGFIELD — In the spirit of giving, Upscale Socks has partnered with Suit Up Springfield for the fourth annual “Suit Your Soles” holiday campaign.

For every pair of socks purchased in the two weeks of Dec. 7-21, Upscale Socks owner Lenny Underwood will make a sock donation to Suit Up Springfield.

“Suit Up Springfield is thrilled and thankful to pair up with Leonard Underwood and Upscale Socks for the holidays,” said Chris Martin, Suit Up Springfield board president. “Upscale will be donating new dress socks to Suit Up that will be available for those who need them to complete their suits. We love the dash of style and boldness that Upscale brings to their apparel, and this will be a much-needed addition for the men who receive our assistance suiting up.”

Underwood added that “we are thrilled to partner with Suit Up Springfield. They provide a very meaningful and important service in our community. The collaboration seemed quite appropriate.”

Purchases can be made at www.upscalesocks.com to support the effort.

Daily News

SPRINGFIELD — As winter begins, Upscale Socks will make a presentation of warm socks to Friends of the Homeless today, Dec. 23, at 1 p.m. at 755 Worthington St. in Springfield.

For every pair of socks purchased between Nov. 23 and Dec. 19, Upscale Socks owner Lenny Underwood is making a sock donation to the organization.

“As a nonprofit behavioral-health agency, we very much value our local community partnerships,” Clinical & Support Options President and CEO Karin Jeffers said. “Upscale Socks is helping our Friends of the Homeless shelter guests stay warm and cared for this winter — and helping them do it with style and dignity.”

Underwood added that “we are thrilled to partner with Friends of the Homeless. Hopefully our socks will bring warmth and happiness to those in need.”

Daily News

SPRINGFIELD — Last spring, MHA started working with Lenny Underwood, a locally-based entrepreneur and founder of Upscale Socks (www.upscalesocks.com), to introduce two different sock designs with mental health themes to tie into the observance of Mental Health Awareness Month during May. Due to the popularity of the ‘Moving Forward’ and ‘Positive Steps’ sock designs, going forward both designs will be included in Upscale Socks’ year-round product line.

Significantly, MHA and Upscale Socks have jointly announced this change to coincide with Minority Mental Health Awareness Month, also known as BIPOC (Black, Indigenous, Persons of Color) Mental Health Awareness Month, which takes place in July.

“At MHA, we know that starting a conversation about emotional wellness and confronting stigma through understanding are important parts of Mental Health Awareness Month, but these are everyday conversations we need to continue having year-round,” said Kimberley Lee, VP Resource Development & Branding for MHA. “Of course we were thankful for the natural tie-in to Mental Health Awareness Month when we introduced the Moving Forward and Positive Steps socks. Now, as BIPOC Mental Health Awareness Month shines a light on the mental health needs of Black, Indigenous and Persons of Color communities, we are especially thankful for Lenny Underwood’s willingness to support MHA by continuing to include our two sock designs in Upscale Socks’ year-round inventory.”

MHA’s mental health themed sock designs are available at these links on the Upscale Socks website:



“Mental health is a topic that doesn’t get discussed enough, especially in the Black community,” said Underwood. “BIPOC Mental Health Awareness Month is a great opportunity for MHA and Upscale Socks to recognize that mental health awareness is not just something we acknowledge for a month or two each year, it’s a year-round commitment. These socks are a great conversation starter that can promote more dialog about mental health and the services MHA provides for anyone who may need support around their emotional wellbeing. As a black man in particular, I know it’s a conversation that needs to happen more often, more comfortably, and with more people in our community. If I can do my part to dispel myths and remove the stigma around mental health, I am happy to help.”

Daily News

SPRINGFIELD — Lenny Underwood, owner of Upscale Socks, is teaming up with the Mental Health Assoc. (MHA) this month with a newly designed line of socks to support mental-health awareness

“I had noticed photographer Lenny Underwood capturing community events, so I knew who he was,” said Kim Lee, vice president, Resource Development & Branding at MHA. “Then I realized Lenny was involved with community panels that tie in with entrepreneurship. He was speaking regularly to groups of adults and also to students. He impressed me, and when someone impresses me from a distance, I try to make that distance go away. I reached out to see how we could partner.”

Added Underwood, “Kim is an idea person, and I like the out-of-the-box thinking she brings to any discussion. Her approaches to mental-health awareness aren’t typical marketing. She brings a serious subject to light in some really creative ways that I totally embraced. Soon we were talking about how we can be in a relationship for the long term, for Mental Health Awareness Month in May, for MHA’s annual fundraising golf tournament in September, and more. She has large aspirations for mental-health awareness.”

Underwood’s sock enterprise began with a dream.

“One night I had a dream I owned a sock line,” he explained. “It was vivid, and I rarely remember dreams, but that night in 2014, I was clear on it. The next day I told a friend. I’m particular about my socks, so I focused on what I dreamt. I followed the business-building process with Spark Holyoke, and a year later, I launched Upscale Socks as a website. It was quite challenging to find manufacturing and turn designs into actual products. Harry Hill, who created my brand and some designs, helped me put legs on this dream to help make it a reality.”

How did the concept of socks to promote mental-health awareness develop? “Organically,” Underwood recalled. “Initially, Kim and I discussed Mental Health Awareness Month and getting something created for that topic. That morphed into a conversation with MHA funders who wanted to make the socks available for golfers in MHA’s annual golf tournament. We identified people who could wear the socks on social media to promote awareness. I pointed out that fashionable socks are one way to reach out to minority communities. Kim shared with me that a majority of MHA staff members are people of color, and she wanted this effort to reflect people they employ who are so vital to the agency’s work.”

Underwood explained a personal tie-in as well: his family has experienced trauma and grief through the unexpected loss of loved ones due to pneumonia and COVID-19. “Those are traumatic events, and some members of my family may still be dealing with their feelings. Fortunately, I have been able to handle it; I feel healed, in part because I understand the importance of getting help from loved ones. For me, having a relationship with God has been vital. I believe formal counseling also can be a good option.”

Personal experience helped Underwood realize that more people could feel healed if not for a barrier that too often stands in the way: stigma. “I see how stigma relates to getting help — or not getting help — with mental wellness,” he explained. “It has been an issue I have seen and heard in my adulthood. But I’m optimistic when I see people in the public eye tell their story, being honest and vulnerable, because folks look up to others who are open and relatable. It helps to create more of a dialogue. For men of color, I think it provides opportunities for unpacking the ‘man box’ and getting to the root issues because, if those issues go unaddressed, they just grow. If there’s a way for us to make a dent in dispelling myths related to trauma, grief, and counseling, I want to help. Especially in light of how COVID-19 has impacted communities, I want to do something to support mental health.”

Working with Lee’s team at MHA, Underwood channeled his energy and enthusiasm into the design and manufacture of new socks. While May is Mental Health Awareness Month, they will be available throughout the year at www.upscalesocks.com and at www.mhainc.org.

“Things I’m doing with Facebook, grants that I applied for, and now also mental-health awareness, these are opportunities that came by making myself available,” Underwood said. “Those who know me know that I show up and bring my true self. I remain humble no matter what, and I want to remain teachable so I am open to someone younger than I am or someone who has more experience that I have, so I can learn from them. That’s why opportunities like working together with MHA are great. So have opportunities to work with Rays of Hope, Springfield Public Schools, Square One, and Educare Springfield, plus a scholarship to honor my late sister. We created a sock for her with a sun, moon, and stars theme, and over 1,000 pairs of socks have been donated so far.”

Underwood is also working on a children’s book that teaches about entrepreneurship. “The story is related to my dream and written in a way that students in fourth grade through middle school and even high school can relate to. Business words like ‘invest’ and ‘capital’ and ‘entrepreneur’ appear throughout, and there’s a glossary to help students understand the vocabulary. The takeaway is, if you have an idea that’s brewing, it’s something you can achieve if you do the work and are consistent.

“There are resources in the community to help, like SCORE, EforAll, Junior Achievement, and the Small Business Administration,” he went on. “No matter what zip code you live in, there’s money out there, and there’s help. What you need to start is entrepreneurial spirit. When you have that and apply it, then it morphs into other things. That’s where I’m at now, with expanding aspirations for Upscale Socks as I move into year five. A rebranding is in the works, and we want to expand by supplying existing stores at wholesale while continuing to build the website. We’ll see what the future brings. Follow your dream and see where it leads.”

Email ‘Picture This’ photos with a caption and contact information to [email protected]

Giving Back

Timm Marini, president of HUB International New England, recently presented a check for $5,000 to the Mental Health Assoc. (MHA). Marini has also committed to a $5,000 donation to MHA for 2020. “HUB International New England embraces the value of the communities where our customers and employees live and work, so we give back by supporting community-focused organizations that do good things to help others. MHA is an organization that we have supported for many years and continue to support because of the important work they do helping vulnerable people,” said Marini (pictured with Kimberley Lee, vice president, Resource Development & Branding for MHA).

Music to Their Ears

Phillips Insurance Agency Inc. recently donated $5,000 to the Berkshire Hills Music Academy (BHMA) in South Hadley, which offers a post-secondary transition program, as well as a long-term graduate program for young adults with intellectual challenges. Its educational model infuses music with an empirically based curriculum to promote skills for independence. Karen Phillips of Phillips Insurance (left) presented the check to Michelle Theroux, executive director of Berkshire Hills Music Academy, at the annual spring concert held at the Bernon Music Center on the BHMA campus.


City of First Socks

Springfield Mayor Domenic Sarno showed his support for Upscale Socks owner Lenny Underwood recently, and bought the first pair of his ‘City of First’ socks, depicting the city skyline and a basketball, representing the Naismith Memorial Basketball Hall of Fame. The socks can be purchased online at www.upscalesocks.com, as well as the Springfield Regional Visitors Center located at 1319 Main St.