The Kentucky Derby is more than a horse race; it’s a celebration of tradition. In the days, hours, and minutes leading up to “the greatest two minutes in sports,” Kentuckians and racing aficionados will sip mint juleps, nosh hot browns, place their bets, and stand to sing “My Old Kentucky Home” alongside the University of Louisville Cardinal Singers. This is, of course, while donning their best Derby attire.
For gentlemen, it’s seersucker sports jackets and linen suits paired with bow ties. For women, it’s vibrant dresses and accompanying headwear. Headbands, hairbows, fascinators, and hats glide atop heads through Churchill Downs. It’s a parade of pageantry that rivals the colorful silks of jockeys. Spectators might come for the run for the roses, but they will stay for the fashion. And the chapeaus are the star of the show.
Inspired by European horse racing events, Meriwether Lewis Clark Jr, a descendant of explorer William Clark of the Lewis and Clark expedition, founded the Kentucky Derby in 1875. At the time, his goal was to bring the same high-class sophistication to America and notably shift the race gambling scene to inviting women to join their husbands. Consequently, their elegant outfits, with striking hats as focal points, were a defining aspect of the race from its inception. Once television gained popularity in the 1960s, these hats became even more theatrical, so they could be seen on screens. Attention-grabbing styles have been associated with the event since.
Hat-making in the Bluegrass State endures with skilled craftswomen who not only preserve this legacy but also reinvent it for a new generation. In Shelbyville, just outside of Louisville, Dori Lewis is a modern-day milliner who creates hundreds of hats annually. What started as a hobby for close friends is now a bustling business complete with a brick-and-mortar shop on Main Street, The Polkadotted Pineapple.
When creating one of her more than 600 annual headpieces, Dori prefers to begin with a blank slate. “Most people start with their dress, which is unfortunate,” she says. “It’s so much easier to start with the headpiece. That’s what they did in the beginning, years ago. Pick that stunner piece you want to wear on your head. You can always wear a simple black or white dress. It’s about the hat.”
She begins by studying a woman’s complexion, eye color, hair style and color, body shape, and stature. “I look at their face. If they put [a hat] on, and it doesn’t show their face, or it’s too dark for them, they don’t need to be wearing it,” she says. That honesty is not only a key to a happy client, but the key to successful marketing. “I want them to get compliments, so they can tell people where they got their hat from. If they don’t get compliments, they’re not going to get to say my name,” she says.
Next comes the fun part: the design. Lewis says she draws inspiration from anywhere and everywhere, and any type of headpiece is exciting to complete. Some creations take hours or even days, while others flow easily. “Sometimes ideas come over you very quickly, and they come together in minutes. You have to sit down right in that moment and put it together,” she explains.
Lewis’s back studio explodes with feathers, trims, faux flowers, and ribbons; accouterments are organized by color for easy pairing. For custom pieces, clients have a bevy of options at their fingertips. “I go through our materials because I forget about some of the things that I might have hidden away,” she laughs. She sources authentic rooster, Lady Amherst, pheasant, duck, peacock, and other bird feathers for her hats.
After all, if it does rain on Derby day, no one wants a flimsy feather ruining their look. Real feathers are meant to be wet, so they retain their beauty and their shape. With a few snips and to-the-trade techniques, these feathers transform to become more sculptural or ethereal based on want and need. They’re then placed, hand-sewn, and glued amid tulle ribbons and faux flowers, resulting in an over-the-top, one-of-a-kind design. And that, says Lewis, is the point. “If they’ve never gone [to the Derby], they’re going to want to be decked out. It’s a glorious sight to me,” she says.
Elizabeth Rosenberg is a fellow hatmaker who sells her designs in The Polkadotted Pineapple. She’s working on a custom hat. She meticulously shapes and cuts adornments, and she gathers pieces of snipped feathers between her fingers. “These little bits? Most people would throw them away, but I’m very thrifty. These are wonderful colors!” She pinches the stems and winds glue and floss around them. The result is a petite puff of plumage. “You can decide where you want to put this little guy to give [the hat] another bit of punch,” she says. “You just have to have the confidence in your own convictions.”
As Rosenberg continues placing ornaments here and there, Lewis contributes a little something, too, “I would run in another pop of color once you knew what you were going to wear, but other than that, I like it!” That stamp of approval might as well be a garland of red roses.
