The incomparable Ms Debbie Matteri and her In Season boutique have been Downtown Bentonville staples since 1991. The Arkansas native began her entrepreneurial journey as a home economics student at the University of Arkansas crafting custom towel wraps for sorority sisters.
I had to pay my way through college, so I did two things,” she said. “I started a towel wrap business and I went to all the sororities each semester. They were nice, plush, towels with an elastic band and I would sew in lace or ribbon and add their monogram on the side. A friend of mine had a fabric and monogramming shop in Tonitown, so she went in with me and we sold them for $19.”
The other endeavor Matteri took on was a popcorn stand. The young student had the innovative idea to set up at Barn Hill Arena and pay Razorback athletes to sell the popcorn in the stands. “I had them wear their team shirt. Everybody wanted to meet them because they were athletes and they were all very nice and friendly.”
Between the two side-hustles, she had raised enough money to get through school and buy herself a house near the square in Fayetteville at the tender age of 21. “That was the 80s, and I think, Fayetteville had maybe 30,000 people,” Matteri said. “It was a little 700-square-foot house with a sign that said, ‘for sale by owner’ and they agreed to finance it for me, but I paid it off early. ”
After graduation, Matteri took a job with JC Penny selling custom drapes, bedding and carpeting out of her car. “Women would make an appointment and I’d drive to wherever they were - this was before GPS - to measure and show samples. It was 100% commission.”
It’s no wonder the retail veteran has sustained a brick-and-mortar retail business for decades. As a young woman, forced to be self-sufficient, she learned to pivot with the times and made the most of the circumstances and resources available to her. Which leads us to the Bentonville chapter of her story…
The new wife left JCPenny to accept a role with Sam’s Club when her husband took a job in Pea Ridge, Arkansas. “I put the house up for sale and we moved to Bella Vista and ran the front desk at Sam’s,” she shared. “I worked for them for five years. It was a great experience because I learned so much about retail; numbers, procedures, policies, things like that. And then I just opened my own store.”
Just like that.
It dawned on me, at this point in the interview, how often overthinking must get in the way of great ideas. Surely, we’ve all thought of a business concept at one point or another, but the dream dies before it has the chance to grow legs simply because starting feels too daunting. If Matteri was intimidated by the idea of starting her own retail business, you would never know. I imagine her having more of a, “Why not?” approach.
With the help of her sister, Bobbi Jo, Matteri opened In Season in 1991 as an upscale women's apparel boutique on the Bentonville square. “At that point Megan [her eldest daughter] was two,” she said. “She would go to work with me every day and my sister would alternate."
“She always loved fashion and always loved working with people,” Materri’s daughter, Megan, shared. “Looking back on it, that was such a risk for my mom to do because Bentonville’s population was maybe 9,000 people and she was selling what would now be, like, $800 clothes."
Megan Matteri left her career in Little Rock to move back to Bentonville and continue the In Season legacy. “I grew up in the back of the store,” she shared. “I had to start wrapping gifts when I was 12.”
Debbie Matteri took a break from retail between 2008 and 2015, when her children were in college. During this time, she managed shops for Mercy Hospitals helping women going through breast cancer surgery. “I did that for years, but I was missing my store. So I learned they were planning to open a 21C downtown, and I found the second In Season location across the street from it in 2015,” she shared. “It was an old buggy barn to the back of a house.”
The In Season on Main Street quickly became a cozy oasis for friends to shop and chat with “Ms. Debbie,” but in 2025, the retail boutique will relocate to, what could be, its forever home to make room for development of A Street.
The pink, victorian-style home on 309 N Main Street was built in 1903, just across from Compton Gardens. It's a new season for In Season, but with the tenacity and dedication of the Matteri women, Bentonville will be loving the retailer for many seasons to come.