Throwing Shade

A new launch, born in Fairfield, during a pandemic? Yes! A brand new company and hat line, SHADY LADY, was founded by Allyson Mandelbaum. This beach-loving Fairfielder wanted a bit of shade that was sporty but also feminine. She just wanted to throw her hair up in a baseball cap, yet she was never really happy with the choices she found—most seemed designed for men or kids. “As a mom of two small kids I rarely have the time or energy, let’s be honest, to wash my hair but still want to look cute,” she says. “So last spring I was on the search to find the perfect hat, but came up empty handed. Hats were either too stiff, too big, had team names on them or adorned with cheesy catch phrases.”

She decided to make her own ideal hat. “If I couldn’t find the hat of my dreams, I had to make it.” She started sketching, looking for soft material and perfecting the measurements. “No more sweaty boy caps.” She used her eye for design to jump on her idea and prioritize comfort and fit. Allyson even added matching designs for kids, because, this mom asks, “Who doesn’t love twinning with their little ones?”

Allyson didn’t exactly start her business from square one—she came prepared. “For the first fifteen years of my career I was a TV producer in New York and L.A. I worked at MTV on shows such as My Super Sweet 16, Catfish and Cribs. I also produced on Wife Swap and Queer Eye for the Straight Guy before landing as director of Unscripted Programming at AMC,” she says. “I loved my career in TV but felt an itch after my second child was born to start my own business.”

From 2017 to 2018 she worked with a partner to create a business that supported local artists by hanging their artwork for sale in coffee shops and stores around town. “I learned a lot from that experience and fell in love with running my own business. I’ve always loved fashion and knew I wanted to start a fashion brand, and it all clicked after I realized there was a hole in the market for women’s hats.”

Now she’s selling Shady Lady hats and credits local support: “Sarah McBrair, who owns Saltwater Boutique, was a huge help in getting Shady Lady off the ground. I told her about the idea over margaritas last summer and she was so encouraging with advice and guidance along the way. She has also been selling Shady Lady hats at her store in addition to Shoe Inn in Westport.” (Of course, shoppers can also find them online at

Because Allyson also lives close to the town’s shoreline, she wanted to address the issue of beach erosion and ocean pollution.

“I grew up going to the Fairfield beaches. I have so many memories of getting Big Gulps at the 7-11 and swinging on the swings with friends or spending my senior skip day at Penfield,” she reminisces. “I’m so lucky now to be able to take my kids to the beaches that I grew up near. The beach for me is therapeutic, it’s where I go to relax, exercise, think and unwind. The beaches in town have given me so much that I had to give back. That is why a portion of our profits each year goes toward cleaning up the beaches and keeping them healthy for many generations to come.”

Four of the six women’s designs ($29 each); also five kids’ styles available ($26 each)
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