How Sweet May Co.'s Courtney Roberts Gets It Done From Her Dining Room Table

By Sara Anne Donnelly
Photographed by Keri Herer
From our December 2020 issue

Sweet May Co., best known for its snuggly-hip hats and hair accessories for kids, started with a glossy-white beginner Singer sewing machine. It was “slow and loud and looked like a plastic toy,” Portlander Courtney Roberts recalls. She’d always wanted to learn to sew, but when a former boyfriend gave her the starter Singer as a birthday gift in September 2017, the timing was tough. Just a week before, she’d had her second child, Emry, and while she juggled caring for a newborn and her school-age son, Aidan, the machine languished in its box.

Four months later, she finally took it out. At the dining-room table, during Emry’s naps and late into the night, she taught herself to make baby beanies, turbans, and headbands that were softer and better fitting than ones she could find in stores. She also mulled big-picture questions. With Aidan, returning to her job as a teaching assistant after six weeks “was heartbreaking,” Roberts says. She didn’t want to do that again. “So I was racking my brain, like, what am I going to do with my life?” She decided not to go back to work, and instead, with Emry as her muse and model, devote her spare time to sourcing silky, stretchy wholesale fabrics and honing her designs. In 2018, she launched her Sweet May Co. Etsy shop, with styles available in newborn through adult sizes. Slowly, through word of mouth and an Instagram feed chockablock with cherubic youth models, sales crept upward, and Roberts saw a new career path. “I started thinking, maybe I should do this.”

These days, Roberts toils on a sleek digital sewing machine in a hallway workspace outside Emry’s bedroom, dreaming up pieces for a devoted nationwide following of parents. Her aesthetic is clean and cosmopolitan, with a palette inspired by New York runways. This winter, for instance, her line is anchored in black and gray with trendy pops of mustard yellow, jewel-toned maroon, animal prints, and buffalo plaid, a Sweet May bestseller. “I try to go for soft, cozy, simple,” Roberts says. “Simple where it’s easy to throw on with any outfit, you don’t have to think about it, and it still looks cute” — which, considering her clientele, is pretty much a given.

Tell us more Courtney Roberts

Where did the name Sweet May come from?

My older child is named Aidan and I call him “Ay” and my younger, Emry, I call her “Em.” So that’s where “May” comes from — Em and Ay. And then I added “sweet” because they are both really sweet kids at heart. That word just defines them.

Your kid-centric Instagram feed is an instant pick-me-up, so thanks for that. Where do you find your models?

Every three months I conduct a search for a couple dozen brand reps, ages newborn to 12. My brand rep families purchase at least one item per month and give me clear, uncluttered pictures of their kids wearing Sweet May. As payment, they receive a discount at the store. It’s been really helpful, and I’ve made some really close mom friends through it. It’s nice to have people like that who genuinely support you and want to see you do well.

You also have an adult line — is it a big part of your business?

I sell the same amount of adults’ hats as I do kids’, actually. A lot of people like to do mommy-and-me sets. My daughter and I do matching headbands. My son is not really into it, though. He’s in middle school, so he’s very particular about what he wears.

What’s coming up for Sweet May?

I’m coming back out with a leopard-print beanie I had last year that people loved. And I’ve gotten some requests for dog bandanas, so I’ve been thinking about doing those with matching scrunchies for the owner because I know people are obsessed with their pets. I feel like it might be something people really like. We’ll see.