Looking for Robb Report UK? Click here to visit our UK site.

A Modern Milliner’s Guide to the Classic Kentucky Derby Hat

Jenny Pfanenstiel is bringing the rich hat-wearing history of the South’s most legendary sporting event into the 21st century.

A Modern Milliner’s Guide to the Classic Kentucky Derby Hat Clay Cook

There’s a long and beloved history behind the Kentucky Derby—and it has little to do with purebred horses. Ever since the ladies of Southern society watched Oliver Lewis cross the finish line at Churchill Downs in 1875, the greatest spectacle of the Derby has been what rested atop the heads of the sport’s most fashionable attendees: flopping garden hats with big velvet bows, bobbed cloche hats dressed in clusters of feathers, and, later, fascinators bedecked with exquisite beads and veils.

The masters behind these extravagant accessories weren’t simple milliners, but artists whose creations were exclusive to an elite coterie. Meticulous in every detail—and vigilant that no design would ever be duplicated—the artisans of the time would burn their hat blocks after the completion of each project. More than a century later, however, just one hat maker retains the tradition and precision of the Derby’s most revered artisans: Jenny Pfanenstiel, a master milliner whose Louisville boutique Formé Millinery Co. is the only place to commission an authentic Kentucky Derby design. Pfanenstiel’s creations are masterful re-creations of decades- and century-old designs, crafted using dozens of recovered blocks she has amassed over time, as well as vintage pearls, broaches, and diamonds from around the world.

Next month, Pfanenstiel will once again hold court as the official milliner of the Kentucky Derby. Muse sat down with the headwear extraordinaire in advance of the legendary event to talk about the rich history of hat-making (and wearing) in the South—and what everyone will be wearing at this year’s race.


Your studio is full of rare fabrics, beads, and handmade flowers. Where do you find them? 

I search high and low all over the world for them. I have a couple of people I have come to know whose family had a trim company in France, and they are slowly selling their supplies off. A lot of them are from the ’20s, ’30s, and ’40s, and we don’t make things like that anymore. They are ornate and detailed and feminine. I’m saving these gems from collecting mold in some warehouse basement.

Sometimes I also come across vintage feathers, and some of them are still in good shape. I love incorporating them into my work. I also have people bring in their grandmother’s brooches or diamonds from family heirlooms, and we will put those on the hat to help personalize it. And I work with a master dyer to make custom prints.


You’re one of the few milliners in the country that uses hat blocks. What are they?

Using hat blocks is a century-old tradition where you mold material by wetting and steaming it over a wooden hat block. Then you dye the material, let it dry, take it off, and then hand-sew the crown and brim together.

Hat blocks are not easy to find. Many milliners used to burn theirs so no one would copy their work. Now I find them at estate sales, and on eBay and Etsy. I also buy them from milliners who are going out of business. People find them in their grandmother’s attic, and they don’t know what they are.


What should people think about when getting a custom hat made? 

First and foremost is comfort—especially for Derby. You’re going to be wearing it for a long time. The horse race is two minutes long, but typically you are at the track for hours. You don’t want to be one of those people whose hat is so heavy you’re taking it off 30 minutes into the day.

I ask my clients questions. Are they the life of the party? Do they like to stand out? Are they adventurous or are they classic? Do they want to blend in? Their answers tell me a lot about what kind of person they are, and that influences what kind of hat I make.

Also, not all of us look good in every type of hat. You should think about your hair length, the shape of your face, your height—all of that plays in a hat. You don’t want to be lost underneath a humongous hat when you are five feet tall.


What is the Derby hat trend this year? 

People are going back to the old tradition of the big rim. I’ve had more requests for them than I’ve ever had. I think it’s the staple of the Derby—a real classic. There are variations of that, where you can get away with a big rim look, but it’s not enormous and won’t swallow you up.

I’m also using a lot of vintage horse-hair trim this year. It’s like lace—very intricate. It’s all different little patterns sewn with horse hair in different colors. It’s just gorgeous.


Should you select your hat or your outfit first? 

I personally think you should start with the hat. Everyone is going to be looking at your hat, so finding the right hat and the appropriate size, color, and shape is important. Anyway, there are so many great outfits out there to choose from—I think it’s easier to find an outfit that accommodates your hat.




Sign Up for Our Newsletter

Subscribe today and engage with dynamic, imaginative and influential women.

Subscribe to Robb Report

Subscribe today and save up to 64%.
Includes FREE digital access!
Subscribe Now