Upscale Socks was founded in 2016 after the founder, Lenny Underwood had a dream one night (Summer 2014) that he owned a sock line business. It was very vivid and specific as he rarely remembers his dreams. He toiled with the idea of launching a new business for about a year until he finally took the leap of faith and began to do some research. After several attempts to learn from local small businesses, pursuing a seven-week startup business program (Spark Holyoke, EforAll) was key in the development of Upscale Socks.


Our collection of styles has grown to be colorful, vibrant, fun, and meaningful socks for the entire family. Since our inception, we have participated in several popup shops, speaking engagements, judged competitions, mentored startup businesses as well-received numerous awards. We have been blessed to be a blessing to local non-profit organizations and schools with our “Suit Your Soles” campaign, where we match a sock donation for every purchase. In addition to our sock donations, we have also given away a college scholarship to a deserving college-bound scholar. Upscale Socks is optimistic about what the future will bring as we continue to grow our brand.


William C. Sullivan Regional Visitor Center
1319 Main Street
Springfield, MA 01103
Hours: Monday-Friday 8:00-4:00 pm
“City of Firsts” style only
Outside the Box Gift Shop
207 Winsor Street
Ludlow, MA 01056
Hours: Wednesdays: 2:00-7:00 pm
Thursdays & Fridays: 11:00-4:00pm
Saturdays: 11:00-3:00pm
ROAM: A Xtina Parks Gallery
230 Mass MoCA Way
North Adams, MA 01247
Hours: Wednesday-Saturday:10:00-5:00pm
Sunday: 11:00-5:00pm

The Green Monkey
1217 Hillsborough St,
Raleigh, NC 27603
Tuesday & Wednesday, 12:00pm-7:00pm
Thursday-Saturday 12:00pm-8:00pm
(984) 200-5682