By Samantha Ratcliffe

With spring finally dawning in the bluegrass, horse racing season in Kentucky is in full swing. But for many, the real race lies in finding the perfect Derby hat before the season begins. Since the very first Churchill Downs races in 1875, dressing for the Derby has been a crucial component. No outfit is complete without a luxurious Derby hat, and Kentucky native and milliner Polly Singer knows that a good hat can make you feel like the sky’s the limit, “I think a Derby hat can be empowering and it’s certainly a great conversation starter. I have so many clients that have met their fiancé at the Derby.”

Since 1993, Singer has been merging New York couture with elegant Kentucky tradition to create one of kind, hand-crafted masterpieces. She is internationally known for her intricate details and authentic Audrey Hepburn-like allure. Not only are Singer’s artsy hats aesthetically pleasing, but each year they help raise thousands of dollars for Kentucky charities. Recently, a Polly Singer Custom Design brought $5,000 at auction for Angel Heart Farm, which specializes in equine-assisted therapy for children battling chronic and life threatening issues. Fifteen percent of every sale in Singer’s newest line, the Hats, Horses and Hope series goes directly to the Kentucky Equine Humane Center. “I’ve always felt that since animals have no voice, we have to speak up for them,” says Singer. The proceeds from hat sales help purchase food and vet care for neglected horses. Each hat in the unique line is dedicated to a special horse Singer interacted with at her time on the KYEHC farm. Three of Singer’s most recent creations will be sold on an eBay auction to support KYEHC on April 1, 2014.

Hat-making is in Singer’s blood. At an early age, her grandmother passed down generations of sewing and crafting techniques to her. “My paternal grandmother was known for her love of hats and fashion. My great aunt Ruby wanted to be a milliner.” Singer even remembers the quote in her grandmother’s yearbook where she admits she dreamed of opening a dress boutique in Paris, France. Though Singer created her own clothes as a child, she didn’t tune into hats as a calling until she worked for a well-known New York City record company.

“One day I was getting ready for work and got a hairbrush stuck in my hair. I called my boss and told him I would be late. Billy Idol was supposed to come into the office that day and of course, I wanted to look my best for Mr. Idol. So I go to work wearing a huge purple velvet hat over the hairbrush. I received tons of compliments.  After designing some simple hats and still getting good feedback, I decided to take classes at the Fashion Institute of Technology in New York.”

Later interning for Patricia Underwood, she was able to work on hat designs for movies like Austin Powers and Speed 2. She says, “I was just so thrilled. Especially with that bubble hat in the opening scene in Austin Powers. That was a bear to do because it had to be blocked over a round object. Patricia Underwood was a great training ground. The downside is that there was no air conditioning and I was there during the summer … in New York, with steam being used to block the hats and iron. I must have lost 15 pounds that summer.”

From hairbrush fiascos to impromptu sweatshops and high fashion couture, Polly Singer’s hat history has finally found a haven in her home state.

Singer describes the work of a milliner as strenuous and tedious, “Blocking hats is very physical. Dyeing straws can be messy.” But the end result is one of a kind, hand crafted artwork made with the finest materials and sculpted in individuality. Each piece is hand sewn, guaranteeing that any hat can be readjusted for the client’s needs. She rises early and stays up late to ensure that each hat order is perfect and the work is never over.

“But there’s never a dull moment,” she admits, “I never know who I will get to work with.  It’s always a surprise.  The people who have horses in the Derby are just so excited. There’s a buzz, which is addicting in a way.”

The addictive buzz that Singer describes is a unified exhilaration experienced by thousands of Derby attendees each year. Singer can remember this same rush as a child watching the Derby in the 1970s, “I remember all the Triple Crown winners. I loved Secretariat.”  Such Derby memories even span to her own backyard where she grew up on the property that used to belong to the horse farm where Kingman, a Derby winner from the 1890’s lived. It was there, in Georgetown Kentucky, where her family still resides on land awarded to them by Patrick Henry for their involvement in the Revolutionary War. Needless to say, this seventh generation Kentuckian knows the fine details of authentic Derby hat creation.

Polly Singer is also a master of bridal veils and custom hair pieces called fascinators. Singer described one of her most memorable fascinator, a heavy horseshoe memorial for the Breeder’s Cup, “The horseshoes had to be welded together and of course, had to be facing the correct way for luck. The fascinator was heavy but the client was a former Miss Louisiana contestant who had no problem wearing heavy things on her head like crowns.” No matter how heavy or daunting the task may be, Singer is ready to take on any challenge to produce a unique work of art. Since the royal wedding in 2011, Singer has seen the trend towards fascinators and saucer hats increase, “It is exciting to see women enjoying wearing a different type of hat.  For more petite women, the fascinators and saucer hats can just look amazing.”

In her line of work, being aware of fashion trends and changes is imperative, “Color is always a big trend. A few years ago, the taupe/nude shoe allowed a lot of women to wear the taupe hats.  That color works so well on most ladies.”

And speaking of color, is it true that your Derby hat must match your outfit? Singer says not necessarily, “It doesn’t have to match, but should really complement.  I always like to see a balance.  If they wear a navy dress, I like to have a touch of navy in the hat.  However I think color is so personal and you really have to see the dress to see how things work.  It’s so exciting when they combine the dress with the custom hat and get a smashing effect.” Her awareness of quick changing fashion trends and determination helps Singer make sure that each hat creation favors the needs and personalities, “I rely on their personalities by seeing how comfortable they are with wearing hats.  As time goes on, my return clients go further each year.  I have had some clients who started with very simple fedoras who are now wearing designs that I never imagined they would want.”

Every custom Derby hat Singer creates has its own story, name, and style. Only a few of Singer’s favorite hats get replicated and sold in bulk, but those that do sell like hot cakes. One of Singer’s favorite international creations was for Lisa Pavin, wife of professional golfer Corey Pavin, “We did a warm taupe hat for her and trimmed it in coral feathers and flowers.  She sent us a dress to work with color wise. It was an Azzedine Alaia and we fell in love with it.” The next year Singer created an altered version of the hat called Captain’s Lady and fueled a massive trend, “Everyone ordered it…I mean everyone.   We started getting silly at one point and wrote a song called ‘Captain’s Lady.’”

Not every  Derby day can be as perfect as the outfits. Singer had a few memories to share, “I went to the Derby in 2009.  It was crazy because our accommodations fell through.  It was raining. We got the last hotel room in Louisville. Finally when I am falling asleep, I hear a drip, drip, drip. Turns out there was a hole in the ceiling. It was like Chinese water torture. We go to the Derby and it was freezing cold. That was the year Mine That Bird won. It was so exciting so see him thunder down that final stretch. We met a client who had Aretha Franklin compliment her on her hat. She was over the moon about it.  Another client got a compliment on her hat from Chelsea Clinton.”

After years of building her own business from the ground up, Singer can feel stretched between her creative callings and creating a steady flow of movable product. However, she has never had a doubt about her true calling towards hand crafted hats, “It’s not for everyone.  Balance is always an issue. I think it fits me because I’ve always loved a challenge. It can be hard to create while doing the business end. I find that frustrating at times but it’s just a necessary evil.  If you don’t do the business side, the hats don’t find homes.”

She’s in the business of helping those hats find homes with clients who want unique hats that speak to them. No matter if her hat is debuting in movies like Austin Powers or Speed 2, shows like The View, or magazines like The Wall Street Journal, Singer is ready to create a hat fit for any occasion.