Kentucky Derby Hats: An Expert's Guide to Headwear at Churchill Downs

Natalie Weiner@natalieweinerStaff WriterMay 5, 2017

A fan with a fancy hat watches a turf race at Churchill Downs Thursday, May 2, 2013, in Louisville, Ky. Saturday will be the 139th running of the Kentucky Derby. (AP Photo/Gregory Payan)
Gregory Payan/Associated Press

"We tend to go big or go home," says Helen Overfield, a hat designer in Louisville, Kentucky, who works hard to convince her clients that when it comes to Derby hats, more is more. "Nothing's too outlandish. People worry about their dress, but no one is going to remember your dress; everyone's going to remember your hat."

Fashion at the Kentucky Derby becomes the primary entertainment for all but two minutes of Derby day—the two minutes during which the race is actually run. The rest of the afternoon is intended for people-watching at Churchill Downs, mostly because of the unspoken mandate that women have to wear hats. As the (quite lengthy) explainer on the official Kentucky Derby site puts it, "The Kentucky Derby is a chance for every female to express her inner Southern Belle." Men's fashion, though less regulated, has some codes of its own. As a non-Southern non-belle, it seemed appropriate to seek the advice of those more experienced in such matters in order to decode the event's opaque dress code.

LOUISVILLE, KENTUCKY - MAY 04: A woman with a fashionable hat walks  near the paddock as she celebrates Thurby in the rain at Churchill Downs on May 4, 2017 in Louisville, Kentucky. (Photo by Jesse Caris/Eclipse Sportswire/Getty Images)
Eclipse Sportswire/Getty Images

"You'd definitely feel out of place if you didn't wear a hat," says Jenny Pfanenstiel, the official milliner of the Kentucky Derby Museum. "People often think of big brims, which will always be a classic Derby look." Pfanenstiel, who is originally from Chicago, used to come to Louisville for six weeks around every Derby to keep up with the demand for hats. Eventually she decided to move south for good, and now she sells hats year-round at her store Forme Millinery. Her client list is about as A-list as it gets: Michelle Obama, Oprah and Madonna have all sported her headgear.

"The wide brim that's wired is pretty classic, especially in sinamay [a very delicate fiber from the abaca tree] with a lot of flowers and feathers and ribbon," Overfield says. She began by making hats for herself when her husband's work in the bourbon industry required a lot of corporate entertaining during the Derby season. Now, she's embellishing hundreds a year for clients around the globe. "Three decades of Derbies," in her words, have left her an expert in the proper garb. "The embellished hats are more indigenous to the Kentucky Derby, not like something you'd see at the Preakness or the Belmont," she adds. The most traditional is red, embellished with roses (because it's "The Run For The Roses," get it?).

LOUISVILLE, KY - MAY 7: Kentucky Derby race fan with a rose hat on Kentucky Derby Day  on May 7, 2016 at Churchill Downs, Louisville.  (Photo by Horsephotos/Getty Images)
Horsephotos/Getty Images

Overfield says she's created hats as wide as three feet in diameter ("But I've worn one that I had to tilt sideways to get in the bathroom stall!"), while Pfanenstiel says her largest hat box is 32 inches across. "You can't have umbrellas at Churchill Downs because it spooks the horses, so if it rains you're all set," Overfield says of her "the bigger, the better" approach to Derby fashion. "Plus, then you don't need any SPF!"

A big hat isn't for everyone though, whether it's because you're short or because you enjoy talking to people instead of colliding with them. "The fascinator is one that's pretty popular now," says Pfanenstiel, alluding to the more delicate, old-fashioned style that Kate Middleton has made widely acceptable again. "You're not bumping into people as much, and it doesn't give you a headache—some hats have so much stuff on them that they're really heavy."

The amount of "stuff" that is deemed acceptable varies depending on where you're at in the Derby fray. "You'll go to the infield and see Kentucky Fried Chicken buckets mounted on beach hats," says Overfield. "Or people who've glued miniature liquor bottles all over their hats. Hats that have an exact replica of Churchill Downs made out of paper mache with motorized horses." With just the tiniest bit of derision, she adds, "It's fun, but those aren't the typical Derby hats—the classic ones you'll see in the clubhouse or the grandstand or Millionaire's Row."

Julio Cortez/Associated Press

Despite the "anything goes" mantra, there are still faux pas to avoid. "A fascinator can be held on with a headband, or elastic that goes behind your head, below your hair," says Pfanenstiel. "Sometimes I see that elastic worn under the chin, like a birthday hat—I can't even imagine how uncomfortable that must be. I have actually gone up to people and been like, 'Can I rearrange this for you?'"

"One of the telltale signs of someone who doesn't know how to wear a hat is if it's on the back of their head like Rebecca of Sunnybrook Farm," adds Overfield. "Really, you need to wear it on your forehead, just a few inches above your eyes—that is the proper way to wear a hat. Horizontal, not vertical."

For men, the options are a little less labor intensive. Consensus was that seersucker, pastels and fedoras are all reliable options.

"You can't go wrong with khakis, a navy blazer, and then a pastel tie or shirt," says Overfield. She also offers some advice that might be familiar to anyone who attended their high school prom: "More and more men coordinate their attire with their dates—the bow tie or the tie match the dress or the hat. That's a nice look that we're seeing more of in the South."

LOUISVILLE, KY - MAY 07:  Professional Football Player Tom Brady watches the 137th Kentucky Derby at Churchill Downs on May 7, 2011 in Louisville, Kentucky.  (Photo by Michael Loccisano/Getty Images)
Michael Loccisano/Getty Images

Tom Brady, noted Derby fan and also a quarterback for the New England Patriots, hasn't taken too many risks in his previous Derby outings—but Pfanenstiel thinks it's time for him to try something new. "I could see him in a seersucker suit and a light cream straw fedora with pink and blue band," she says. "You come to Derby, and you take risks with your fashion. He'd fit right in."

The process of creating unique Derby fashion isn't simple. As Pfanenstiel puts it, "My Derby starts when Derby ends"—her year-round dedication makes more sense when you consider she's crafting about a thousand hats by hand. Each one takes three to four days—she works on a few at a time—and since she's a milliner, she's crafting each piece from scratch.

"My hats have sold into the $2500 range," she says of the most expensive, couture pieces she creates—most are a good deal lower. "Here in Louisville, it seems like everyone comes out of the woodwork and makes hats—even gas stations sell hats. There's a difference between buying hats from China and gluing stuff on, and what I do. I take great pride in keeping the craft of millinery alive."

Overfield describes herself as a hat embellisher who works to keep her prices low—"more for Joe Everybody," in her words. It's a side gig, but she still produces hundreds of hats a year in the $140 to $180 range.

Embracing the tradition of the Derby hat may seem a little tricky to those not accustomed to wearing something large and colorful on their head, but both designers insist the risk is worth it.

"Sometimes people are skeptical that they can pull off a hat, but when they get to the track, they realize: 'Oh, my hat is actually so sedate! I wish I'd gone bigger and bolder and brighter,'" says Overfield. "If it's just plain, someone's gonna say, 'Where are your embellishments?!" You need a flower or a feather or a bow or some netting or some tulle."

"Otherwise, it's not a Derby hat—it's just a hat."

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