Orleans Milliner Brings Back Racehorse Fundraiser, Looks Ahead To The Future

ORLEANS – One of the first books that Sally Steinmann read as a child was “Black Beauty.” 

 “I sort of had that, and still do have that perspective of animals, like us, having stories, lives, families, emotions,” she said.

 A native Cape Codder, Steinmann’s life has been driven by her love of art, nature and, yes, horses. For almost 30 years, those elements have melded seamlessly into her work through her business, Maggie Mae Designs. A seasoned milliner, Steinmann has made a long career making custom women’s hats, including those for celebrated horse races such as the Kentucky Derby and England’s Royal Ascot. For someone with a life-long love of horses, it’s the perfect creative endeavor.

 “I just seemed to have kind of an affinity for it,” she said. “I just started getting customers. It was mostly Derby, brides, mothers of the bride and groom, that sort of thing. But it was real validation very quickly.”

 Following the tragic death of the champion thoroughbred Barbaro in 2007, Steinmann became motivated to more directly support racehorses in retirement. The following year, she partnered with Old Friends, an accredited aftercare facility for retired thoroughbred racehorses in Georgetown, Ken.

 For 14 years, Steinmann organized “Hats Off to the Horses: The Road to the Derby,” an annual fundraiser in which a collection of Derby hats, each customized for a specific horse at Old Friends, was auctioned off in support of the facility. The event raised more than $45,000 for the facility before going on hiatus in 2022.

 “I wanted to do something more,” she said. “It was that old horse passion that kickstarted again.”

 After stepping away from the fundraiser to help care for her mother until her passing, Steinmann has now brought “Hats Off to the Horses” back. She’s also looking forward to some other future projects with Maggie Mae Designs.

 Steinmann grew up in a family that encouraged the arts, and she spent much of her early life testing the creative waters. Initially she wanted to study theater, but after one semester at the University of Massachusetts Amherst, she returned home, where she took on a number of different jobs.

 “I tried every single kitchen, house cleaning, whatever job I could,” she said. “I was so miserable. My mom would joke about it. ‘That’s where you spent 45 minutes at the job. That’s where you spent about five hours at that one.’”

 After attending classes at Cape Cod Community College, Steinmann was accepted at Wellesley University, where she studied women’s studies, photography and video. The school helped rekindle her creative spark. Steinmann, who at the time was an older student on campus, said she took particular inspiration from the school’s younger students. 

But it was when she returned home again after graduation that she found the creative avenue that would launch her career. Her mother gave her a pattern for making felted wool hats. Before long, she was making custom hats for clients including the late actress Julie Harris.

Steinmann tried selling her hats wholesale, but said she wanted more of a connection with the people who were buying her products.

  “I don’t even know who they are, I don’t know how the hats are being taken care of, how they’re displayed,” she said. “I’m a wholesaler, and that just never was me.”

 After taking a business class in Eastham that taught her the basics of running a small business, Steinmann launched Maggie Mae Designs in 1998. By the early 2000s, she had gotten out of wholesale work completely in favor of making custom hats full time.

 As a custom milliner, Steinmann collaborates one-on-one with her clients.

 “That’s the connection that I didn’t have with wholesale,” she said. “I was meeting my customers, they were meeting me. They were getting their own milliner who at the drop of a hat they could write to, call, message, send swatches to, send photographs. It was just so much fun.”

 The personal nature of her work also carried into “Hats Off to the Horses.” Steinmann started by creating six customized hats a year, a figure that later got scaled back to four. The work, she said, required familiarizing herself with each horse by any means necessary.

 “I have to get to know the horse, and I’m doing it all long distance,” said Steinmann, who now lives and works out of her home in Orleans. “I’m going online and watching races. I’m watching them after their races, I’m watching them with stable goats. I’m interviewing people who know them at Old Friends or beyond that. Talking to owners and trainers if I’m lucky enough. Just soaking up as much as I could.”

 Steinmann had started to work on her line of hats for 2023, but she bowed out to take the time needed to care for her mother. 

 “Looking back, I wouldn’t do anything any differently, because it was my mom,” she said of her time away from her work. “At the same time, there was a heartache from being so far away from my art.”

 But through the hiatus, Steinmann said she found renewed inspiration from her native Harwich. She picked up her camera and started documenting what she saw daily. The experience not only kept her on the Cape (she and her husband had contemplated a move to Maine), but helped inform a new direction for her work. In 2025, Steinmann rebranded the fundraiser as “Hats Off to the Horses, From Cape Cod To Kentucky.” 

 “As part of a rebranding of my business, I want to crystallize my story through the fundraiser as a custom milliner from Cape Cod who happens to love horses and wants to make a difference in their lives,” she said.

 Beyond the fundraiser, Steinmann is also looking at a new line of custom hats tailored more to the Cape. That includes different fabrics and colors that tie in more closely to the region’s natural beauty.

 “I still hope that I always get Kentucky Derby customers, but I was doing it almost exclusively at one point,” she said. “So the colors, all my fabrics, were bright colors. All of a sudden, I was like ‘I need to create the world that I already know.’”

 After some professional twists and turns, Steinmann has managed to build a business that satisfies her many passions. But while she’s successfully made Maggie Mae Designs in her own vision, she said her work is far from complete. 

 “I hope I never have that feeling,” she said.

 This year’s fundraiser runs up until the day of this year’s Kentucky Derby on May 2. For more information, visit hatsofftothehorses.maggiemae.com.