Writer Nicole Letts visited ShelbyKY and met with Polkadotted Pineapple owner Dori Lewis, who expanded on the process of making the picture-perfect Derby hat. 

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. 

A milliner works with vibrant blue feathers, crafting a decorative headpiece while surrounded by various materials and tools on a table.
Image: Nicole Letts

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.” 

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