Not Win, Not Place, but Show

LOUISVILLE, Ky. —  Fran Dye is 80 years old and a bit weary from her cross-country plane trip, but when she hands Wayne Esterle a white straw hat, she breaks into a jig.

“We’re going to go a little fancy!” she trills.

Dozens of hats are piled in Esterle’s workshop; he’ll be up past midnight adorning each one with flowers and feathers and yards of tulle ribbon. Still, he manages a grin for Dye. “You got it!” he tells her. Then he picks up his glue gun and a creamy silk hydrangea.

So much frou-frou, so little time.

In an annual rite of flamboyant excess, hundreds of women have mobbed Esterle’s design shop all week, clamoring for him to make them the biggest, most outrageous hats he can dream up -- Kentucky Derby hats.

In the rest of Louisville, in the rest of the country, Derby fans pore over racing sheets, analyzing whether Action This Day can pull an upset win over The Cliff’s Edge.

In the hat shop, women debate whether their fake flowers should be tinted peach or apricot.

“Does this make me look like a lampshade?” Cathy Udall asks a friend, trying on an orange hat shaped a bit like an old-time hair-salon helmet drier.

Day blurs into night as Esterle tacks velvet trim, spray-paints silk peonies, coaxes purple asters to cascade just so down the brim of a coy bonnet.

His thumb is stained sea-foam green. His fingers are raw with glue-gun burns. Meals go uneaten, cigarettes unsmoked.

Taking up Dye’s hat, he shapes turquoise netting into a pert bow, then tucks in teal marigolds that pick up the precise shade of the shoes she brought from Corona Del Mar to wear at today’s races. She left them in his workshop, for inspiration.

Another customer has left him her skirt. Esterle dissects a faux daisy and arranges the petals until they match the embroidered pattern perfectly. He’ll spend more than an hour on this one order, adding a bloom here, twisting a leaf there, until the hat looks glamorous and gaudy at once.

“We marvel at our clients’ taste,” Esterle says.

“Their good taste, I should say,” he adds hastily. “Certain people can put on a hat that’s way over the top, and if they have the right attitude, they can pull it off.”

At Churchill Downs this afternoon, there will be attitude aplenty.

Wearing hats to the Derby is a ritual as cherished as singing “My Old Kentucky Home” while the thoroughbreds parade to the starting gate.

A century ago, the hats were practical, designed to shield fair complexions from the sun. Now, they’re an excuse to strut. Fashion tip of the day: Big is good. Bigger is better.

“Any other time of the year, you’d feel like you were in costume,” says Debbie Myers, a banker from Anchorage, Ky., in her early 40s. “Or you’d feel like you were a package all wrapped up with a bow.”

At the Derby, however, “if you show up without a hat, all day long people will ask you where your hat is,” says Anessa Arehart, who works for the Kentucky Museum of Arts and Design. “It’s easier to wear one than to try to explain.”

In recent decades, Derby millinery has divided into two distinct camps.

The college-age crowd that floods the infield -- the grass oval in the middle of the track -- tends to favor tank tops, cutoff jeans and mud wrestling between races. Their hats match the spirit of their $60 “cheap” seats, topped with toy horses or beer cans.

In the luxury boxes -- where a seat can cost more than $500 -- the attire is cocktail-party swank. There’s no official dress code. But the tug of tradition is so strong, there might as well be. Men can get away with going hatless. Women can’t. And in fact, most don’t want to. Many cheerfully admit that they have more fun watching the hats than the horses.

“It’s like a day at the beach, where you’re checking out everybody that goes by. Only instead of, ‘I can’t believe that guy’s wearing such a tight Speedo,’ at the Derby, you’re like, ‘How elegant! Isn’t that hat amazing!’ ” says Tony Terry, publicity director for Churchill Downs.

Drawing those oohs and aahs can cost anywhere from $50 for a department-store hat to $1,500 for a designer original.

If you’re a Derby regular, that’s an annual expense: No one wears the same hat two years in a row.

“Your outfits change,” Myers explains. “And your friends would notice.”

Some women do wear their hats to church, or weddings, or garden parties -- or even to opening days at California racetracks. A few hang their Derby hats on their walls as art.

But most of the eye-popping creations end up in closets. The flamboyant style that goes so well with mint juleps just doesn’t hold up outside Churchill Downs.

“Let’s face it,” Terry says. “If you wore these hats anywhere but the Derby, they would look ridiculous.”

That’s why Esterle spends most of the year running a downtown floral shop. He picks up his glue gun for just 10 days each spring, when he takes over a vacant shop at the Executive West Hotel near the airport, where many racing fans stay.

He drapes the walls with black curtains, installs shelves and mirrored pedestals, floats a few feathered boas over the counter -- and the Hat Shop is open for business.

The store bursts with color. Here’s a lime-green bird’s nest covered in fluorescent-bright down. There, a purple saucer decked with cloth ruffles. On this pedestal, a red chapeau sprouts huge black latex magnolias, so shiny they almost reflect. Esterle has designed most of these hats himself, though he purchased a few ready-made from fashion shows.

Staying open as long as the customers wandering in are sober -- which can be as late as 11 p.m. -- Esterle sells a few dozen off-the-shelf hats each year.

But most of his sales come from his cramped corner workshop, hazy with too many aerosol sprays of dusty rose and aqua paint.

Perched on a stool, a Styrofoam head nearby to serve as a model, Esterle creates about 300 hats in the week leading up to the Derby.

Few customers give him specific instructions. They just show him their outfits and let him pick and choose among the hot-pink ostrich feathers, the rhinestones, the crystal baubles, the 700 stalks of flowers, the 40 shades of paint, the 500 yards of tulle ribbon in two dozen riotous colors.

One longtime client, Bonnie Gates, 69, brings five outfits -- dress, shoes, purse and all -- when she drives up from Morristown, Tenn. She lets Esterle pick the one she should wear. Then he creates a matching hat guaranteed to stand out in the race-day crowd of 150,000.

This year, he presented her with a black hat, nearly two feet across from brim to brim, adorned with regal vines of purple wisteria that drifted down almost to her shoulders. At $500, it was his most expensive creation of the season. Most of his hats run $150 to $350.

Gates -- who admits she goes to the Derby for the socializing, not the sport -- was thrilled with Esterle’s effort: “He’s the greatest, just the greatest.”

Bruce Meyer, 68, has heard that refrain many times.

Every year, he and his wife, Barbara, drive to the Derby from their home in Flora, Ind.

Every year, she tells him she’s brought an old hat with her, so she won’t need to buy a new one.

Her resolve lasts about as long as it takes to walk from the hotel registration desk to the Hat Shop.

“Oh, I love this!” she says, trying on one of Esterle’s designs, a sheer black hat blooming with red roses.

“How ‘bout this?” her friend Marijo Driggs, 62, calls out. She has on another Esterle original, a brown hat with quill-like feathers poking out at odd angles, like a rumpled porcupine. “What do you think? Is it too much?”

“Oh no!” Meyer gasps. “It’s perfect!”

Her husband stifles a laugh.

“Every year, they come here early and think they’ve found the perfect hat. Then later in the week, they find another one that’s more perfect. And then another one. By the end, they’ve each bought three,” Bruce Meyer says. “The way they strut their stuff, you’d think every one was a movie star.”

He sighs. “If it looks good and it keeps Momma happy, that’s good enough for me.”

Esterle, 46, has been interested in floral design since he began fishing discarded bouquets from the cemetery trash bin as a teenager so he could practice arranging. But he’s never formally studied fashion design, and stumbled into the hat business by accident.

In the mid-1980s, his floral shop was located in the Executive West. One year, Esterle trimmed a few hats to decorate the windows for Derby week. They were intended for display, but women begged him to sell them.

Sensing a market, Esterle trimmed two dozen hats the following year. He sold out within days. Between the hat shop and his fresh-floral business (which employees run while he’s busy with the hats), Esterle makes 15% of his annual income in the week leading up to the Derby.

He’s come to think of those frenetic 18-hour days almost as a family reunion.

A former floral shop employee, Judye Fravert, returns from Oklahoma City every year to work the counter at the Hat Shop.

Customers come back year after year, too. Esterle knows many of them well enough to nag them unabashedly.

Huddled in the back with Fravert one afternoon, he frets that a favorite client is planning to wear black sandals with a cream-colored linen suit.

“She says she’s not going to buy shoes to match,” he whispers. “But she will if we tell her to.”

Later, he frowns as his part-time assistant, Harriette Miller, trims a hat to match a bright floral jacket. The customer has asked for flowers in red, gold and white.

“Those look like team colors,” Esterle says unhappily. “It really does need some purple.”

Fravert pokes her head in the workshop to remind him that the customer specified no purple. But already, Miller is gluing a few silk violets to the brim.

“She’ll get over it,” Esterle says.

Most of his customers do. They have long since learned to trust his instincts.

“He makes the hats so beautiful, you feel really good when you wear them,” says Anne Burke, who breeds racehorses in Huntington Beach.

Burke ordered her first hat from Esterle five years ago. A broad-brimmed beauty, it was entirely covered in red rose petals, so it looked like a giant open bloom. Her photo made the Louisville paper that year.

She’s been back to the Hat Shop every Derby since, demanding evermore intricate creations.

“I’ll tell you,” she calls out, as Esterle lifts his glue gun once more, “this really is a ball.”