Style with a Smile

When I was growing up, back-to-school shopping meant a pack of No. 2 pencils, a black and white composition book and maybe a pair of tennis shoes or Mary Janes. Now, it’s mini-erasers shaped like pandas and elephants, fidget spinners and light-up Skechers. The basic accessories of the ’60s and ’70s are over, and kids clothing and toys have gotten shinier and more complicated.

Former Andover resident Caroline Leed is bringing back classic fashion styles for young girls (an eventually young boys) with her clothing brand, Smiling Button. The brand offers eight dress styles: The Pinny is based on the pinafore; the Tuny is like a tunic; the Sunday has little cap sleeves perfect for anything from a morning at church to an afternoon picnic.

“The brand has a little bit of a retro feel in the sense that I really want that mother or grandmother or whoever is buying the dress to remember, ‘Oh,
I had a dress like that when I was a child.’ The prints themselves are very modern, but the styles are classic,” Leed says. “It’s fun because it excites not only the child who is wearing it, but also the parents who are buying it, or the grandparents who are buying it.”

As a kid who wore overalls and Converse sneakers one day, a velvet dress the next, Leed loved exploring different outfits and seeing which held up best during a day of play. She is inspired today by childhood memories, and incorporates them in her design work — tiny ballet dancers and zoo animals are common motifs.

The Smiling Button style is exemplified by classic design. These 100 percent cotton dresses are meant to be fun, colorful and practical for active children. Smiling Button is the brainchild of former Andover resident Caroline Leed, who finds inspiration for her patterns in the New England landscape, vintage toys such as yo-yos and her enthusiastic clients. Photography by Kevin Harkins.

“I loved yo-yos so much, so one of the things we do is once in a while we’ll slip a yo-yo into one of our packages. Today, kids are so bogged down with technology and iPads, and I just think it’s fun to bring back the classics.”

When creating a new print, Leed makes sure to go to her clients for additional inspiration. She’ll make friends with the girls and their mothers at photo shoots and learn which animals, colors and activities are their favorites. Dancing flamingos, colorful balloons and pink polka dots cover the 100 percent cotton dresses, which are easy to throw on, run around in, and toss into the washing machine at the end of the day.

Leed, who now lives in Boston, says her prints are often influenced by New England. The summer 2017 collection featured navy blue crabs, smiling sharks and tiny anchors. Blue and red gingham and seersucker are featured in several of her Cape Cod and Maine photo shoots. All the clothing is made at a Massachusetts facility about an hour from Boston, which Caroline visits about once a week to check in on production.

Smiling Button dresses have spread across the U.S. and are now offered in 45 boutiques internationally, including Bloomingdale’s. Currently, the brand only produces clothing for girls, but Leed says boys clothing is on the way, with a one-piece Jon Jon ready to launch next summer. She plans to extend her line with cardigans, shorts and a terry cloth beach hoodie by next summer. Her goal is to make Smiling Button an international brand.

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