How do you dress for the fair? Do you lean into being a fashion girl or just sport the brand merchandise?
Comfort is key. I’ve got a uniform: our bright yellow Sweet Martha’s employee tee paired with vintage fatigue pants, old Dickies, or Patagonia Baggies when it’s hot. This year I ordered some yellow Human by Nature shorts to go with our color theme. We also have an array of Sweet Martha’s merch—hats, sweatshirts, shorts—so I’m usually decked out in some kind of SMCJ gear. I also swear by New Balance sneakers for comfort and style.
Tell us a little about the Sweet Martha’s merchandise that always sells out! How did it come to be and who designs it?
Before we ever had an official merch line, we did a one-off T-shirt with Vampire Weekend—the collaboration came about after Ezra Koenig and Jake Longstreth had my mom on their podcast, Time Crisis, which was adorable. We sold the tee when they toured through Minneapolis in 2019, with proceeds going to the St. Paul Public Library, which my mom is passionate about supporting as a former educator. They even brought Martie out onstage during the show to say hello to the crowd and played “Martha My Dear” by The Beatles as she walked off.
Then in the summer of 2020, when COVID canceled the Minnesota State Fair and we suddenly had some extra time on our hands, we officially started making Sweet Martha’s merch. We began by tie-dyeing tees with our logo on them, and customers loved it. After such an overwhelming response, we decided to grow the line the following year, with guidance from my dear friend Aaron Levine, who I worked closely with back in the day at Club Monaco.
We’ve also done some incredible collaborations since then, including the embroidered cookie shorts we made with Petrified Good—a nod to the Grateful Dead’s dancing bears. And we’ve continued collaborating with bands that come through town, like The Black Keys and, most recently, LCD Soundsystem, with proceeds always benefiting the St. Paul Public Library. It’s been so much fun being able to combine my love for the family business with some of my favorite bands.
What will you miss most about the Minnesota State Fair?
Our employees! When you hire over 700 people, you get so many different personalities. The majority of our staff are between 16 and 21, and it’s so much fun getting to hang out with them and learn what’s trending and popular these days (FYI, “bet” is still a thing). Everyone brings such different, interesting skills to the table.
Our senior staff are just as essential—many take time off from their regular day jobs or come in after work just to help us run the ship. For example, my aunt Mary is a public school teacher by day and comes in to help at nights! Not all heroes wear capes—some wear aprons dusted in flour. Relative or not, these people are my cookie family, and we couldn’t do it without them.
This interview has been edited and condensed for length.
See pictures from a typical day at the Minnesota State Fair for Olson and the rest of the Sweet Martha’s team below.