Meet Polly Singer, an Etiquette-Savvy Kentucky Milliner

As celebrations for the Kentucky Derby’s 150th anniversary gear up, we’re spotlighting acclaimed Southern milliner—and teatime aficionado—Polly Singer of Polly Singer Hats, Teas and Events. From classic caps to Derby dazzlers, Polly designs distinctive millinery couture for all occasions. Read Polly’s story and her tips for selecting the perfect chapeau.

Polly Singer is no stranger to wearing multiple hats—all while crafting and selling them. After years spent in jobs that spanned the music industry, nonprofit organizations, and other realms, the acclaimed designer has found her calling in artful headwear and complementary ventures such as tea, etiquette, and travel.

While living in New York City in the 1990s, Polly took millinery classes at the Fashion Institute of Technology (FIT) after a hair catastrophe led her to don an over-the-top hat that elicited unexpected raves. “It was funny the way people reacted to the hat. They were like, ‘Oh my gosh, that’s so cool.’ It just hit me that hats are wearable sculptures,” says Polly, whose handiwork has since been displayed at Louisville’s KMAC Museum and New York City’s American Craft Museum.

Polly has gotten to know her client base even better after becoming a certified etiquette consultant for afternoon tea and facilitating classes. “Tea events give ladies a chance to wear their hats and connect—kind of an escape to dress up and meet new people,” she says.

 

Fostering a spirit of community is central to Polly’s passion, and she nurtures that by hosting special events. “It’s about the hats, but it’s also about the people,” she says. “When they wear one of my hats, I want them to feel beautiful—like a million dollars.”

Polly Singer’s Expert Hat-Styling Tips

Polly has fine-tuned the art of effortlessly complementing a stylish wardrobe with a picture-perfect hat. Here are some of her tips and tricks to sporting a couture hat with confidence.

 

For indoor events: Don a hat that’s a bit smaller in size to appropriately fit the space. A large hat with a wide brim is uncomfortable to wear when sitting at a cramped table. Polly recommends wearing a cloche—specifically, a vintage profile cloche—fascinator, or saucer hat for this type of occasion. If you are drinking tea, avoid anything with veiling, because it will prohibit sipping the beverage.

 

When attending outdoor gatherings: Choose a larger hat with a bigger brim for both sun protection and a beautiful, romantic look. If you’re sitting outside on a warm summer day, you can wear a hat with a 5-to 6-inch brim. Personalize your hat by adding a lovely scarf, a vintage pin or jewelry, and/or fresh flowers, which can be secured with floral tape and a pin.

 

For any occasion, balance is key. If you’re wearing a floral dress, a simpler hat would be appropriate. Choose a hat that pulls in a few of the pretty colors from the dress. Less is always more when it comes to accessorizing. The easiest way to incorporate a magnificent hat into your ensemble is to select a solid color for your outfit. You can do a lot more with your hat or fascinator without a competing print, and you can properly show off your beautiful and colorful creation with lots of pizazz.

 

Consider sustainability and affordability. When purchasing a designer hat or fascinator, choose one that is highly versatile and can be utilized for various events. Add-ons, such as feathers, flowers, ribbons, and pins, can be easily swapped out to produce a hat that looks brand-new but without the expense of buying an entirely new accessory.

 

Read more about Polly Singer and find a plethora of Derby-themed inspiration in this Derby Celebrations special issue, available for purchase on newsstands and online.

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