Steinmann's spark grew from a simple pattern for a felted hat that her mother gave her. As a child, she made clothes for her stuffed animals, and later in life, she sewed her own clothes. After trying the pattern, she began to sell hats locally at a gallery shop on Cape Cod. Now, her site delivers to people all over the world.
From Michigan to Idaho and Ohio to Cape Cod, they craft custom hats for women they may never meet in person.
It means e-mailing photographs and mailing swatches of outfits to match the hats, hours of chatting on the phone and even using software to "try on" a hat (a feature Siverson's website offers) or a virtual "sitting room" with everything from a "millinery mugshot" to photos of the hat in progress on Conti's site.
Siverson and Steinmann chat with their customers, listening for the nuances in their voices. The conversations reveal the kind of hat they want, from reserved to loud and crazy. Because a bespoke hat is such a personal thing, they want the finished product to project the customer's personality.
After investing anywhere from three weeks to an entire year into the making of a hat, a connection forms between the milliner, eager to hear her customer's response, and the wearer, who usually picks up the phone as soon as the box arrives, squealing.
"It is so amazing to pop it into the box after that kind of involved process," Steinmann said. "I not only have a relationship by then with the customer, but the hat as well."
Like the other milliners, the hats featured on Henning's site aren't "sitting on the shelf" and ready to ship. Rather, the photos are inspiration for what customers might want to build. And just about every client asks, "Have you already sold a hat like this for the Derby?"
Inspirations for the hats come from their customers, but Conti is especially influenced by the glamour of 1930s and 1940s millinery. Because she is "creating all the time," Conti can even find inspiration by looking at a bowl or a lamp. For 19 years, she has been creating almost all her hats by hand: "It makes the stitches less easy to see."
Helping a woman find her perfect hat can be inspiring, as veteran Derby hat seller Lucille Jackson, owner of Hunter's Hatters in Lexington, Kentucky, knows well. The 80-year-old has been in business since 1984, but her shop could close after the Derby because her older, loyal customer base has shrunk due to illness and old age.
Although she orders 95% of the hats in her store, she customizes most of them to suit the individual personality of her customers, from one-timers to regulars. "I would rather see a lady happy in a hat that completes her wardrobe than to do a lot of things, honey," Jackson said
But she remains optimistic that she'll stay in business, because Jackson offers the kind of personal, by-appointment service that isn't available in department stores today. She sits down with her "ladies" and helps them determine their color, style and "hattitude," something the milliners are well-versed in spotting.
"You've got to know how to wear it," Jackson said. "You have to have an attitude for a hat, and that creates a hattitude. If you don't have an attitude about the hat, it doesn't mean anything, like a stick pin -- it's just there. A hat is a true accessory and so important, because it makes a woman look so beautiful and feminine."

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