Brimming with Beauty: Polly Singer Brings Couture Hat Design to the Bluegrass

Updated: Oct 4

Article Written By Nikki Edds

Polly Singer removed her navy wide-brimmed hat and presented it across the table. She carefully flipped the accessory over and ran her index finger over each small detail, meticulously describing where she acquired the hand-stitched crystals and felt lining that decorated the custom piece.


The Kentucky native has been designing since 1993 and is the proud owner of Polly Singer Couture Hats. Her attention to detail has earned her the title of Best Haute Couture Hat Designer in the United States by Luxe Magazine in England as well as features in Southern Lady, Tea Time, Kentucky Monthly and more.


Singer’s career as a world-renowned milliner began while working in the chairman’s office of EMI Records in New York City. While she enjoyed working with high-end musicians and celebrities, what she missed most was working with her hands, Singer said.

Inspiration struck in the form of a bad hair day before work. Instead of letting the mini-crisis delay her, she opted to wear a star-studded hat–one that received countless compliments. Given her background in sewing and growing up attending 4H camps, one of her friends suggested enrolling in the millinery program at the Fashion Institute of Technology (FIT).


Singer was fortunate enough to already live in New York City when she began her education at the prestigious school, allowing her access to the more affordable in-state tuition. There, she studied under professors that had previously designed hats for Jackie Kennedy or worked with luxury fashion houses like Balenciaga. While intense, she said she learned a lot from the experience.


“They were very much perfectionists. They would actually come around and examine your stitches and if your stitches were off you would have to fail,” she said.


During her final year, Singer created a collection of hats based on Audrey Hepburn. Her hats were inspired by Hepburn’s timeless films such as Breakfast at Tiffany's and Sabrina. Her designs caught the attention of Patricia Underwood, who enlisted Singer as an intern. As an intern, she assisted in the creation of the hats for the Austin Powers movie.


“It was neat to see how something of that level works,” Singer said.


While the New York City fashion and design scene may be all-consuming, Singer was soon drawn back to her roots in Kentucky. Through a job she had, she received a postcard about Kentucky Derby Hats, sparking her interest in the market. From there, her business was born.


When creating customs pieces for clients, Singer uses the “Singer Method.” This method ensures that every client is happy with every hat, every time.


“With a new client, you're really trying to determine what their comfort level is. Are they more tailored or are they casual? What are their favorite colors? And you have to look at their face too,” Singer said. “It's pretty involved.”


Clients of Polly Singer Couture Hats receive a personalized experience from start to finish. Singer not only accounts for their general personal taste but also the outfit they will be wearing to the event. She often has her clients send her pictures of themselves in their outfit, she said.


“I want them to feel comfortable. A lot of times for Derby, it's a person that needs to go for work or something like that and she hasn't worn hats so she's a little nervous,” Singer said. “I get people that are nervous and then I get people that want over the top. As time goes on, they want more crazy.”


To adapt to change in taste, it's very important to Singer that her hats are sustainable as well as customizable. She can take a hat she made for a client years ago and add new feathers, beads, colors, or anything else her and her client dream up together to make sure the piece is perfect for any event.


Singer once designed a hat for an actress that was headed to the Breeder’s Cup when it was hosted in Louisville. This particular client wanted horseshoes on her hat. She wanted them to be real and she wanted them, of course, to be facing upwards for good luck.


Singer approached the challenge as if working with a sculpture. Not only did she have to figure out a way to get the horseshoes to stay upright, she had to accommodate for the weight of them on her client's head. She eventually enlisted the help of a local welder to make the hat come to life.


“It was unlike anything I've ever done, it was really out of the box and I really like those kinds of assignments,” she said.


In addition to customs, Polly Singer Couture Hats sells ready-to-wear hats on their website and has pieces for sale at Bella Rose in downtown Lexington. Singer has also designed hats for charity with one of her pieces recently raising $5,000 at a live auction for Angel Heart Farm.


When she is not designing hats, Singer fills her time exploring her love for tea and etiquette.


“As a creative person, you're always looking for new things to do,” she said.


In February of 2021, Singer was contacted by a representative from Southern California School of Etiquette and Protocol asking if she had ever considered tea etiquette. The representative suggested that it would fit very nicely with her hat business. Singer was immediately intrigued and soon partnered with Chef Ouita Michel to do a hat tea at the award-winning Holly Hill Inn. Singer said the afternoon was an incredible success.


“It was really neat the way everyone was coming out. People were just so wanting to get together with friends, dress up and have tea,” she said. “It's very much a bonding thing.”


Singer has been in a tea group since 2008 and has recently created her own brand of hand blended artisan teas.


“Tea is all of the senses. The taste, the smell, the warmth, the touch, it just incorporates a lot of beautiful things,” she said.


Singer has worked for decades to curate a life of these kinds of beautiful things. Whether that be in the form of high fashion hats, luxury teas, or well-organized events with like-minded women. Singer is currently prepping for Breeder’s Cup and Keeneland Fall Meet. To become a client of Polly Singer Couture Hats this season visit her website or her Instagram @pollysingerhatsandteas.