The Most Ornamental and Ornately Designed Hats for the Kentucky Derby

Kentucky Derby Hats

Photo Courtesy of Shutterstock

Sports and fashion rarely collide, so when they do, it’s kind of a big deal. One of those rare times is at the Kentucky Derby—and we can’t help but get excited.  Hats are the epitome of the event; half the time we don’t even realize horses are running around the track—we’re too busy absorbed in the sea of brightly-colored, floral, larger-than-life toppers. Kentucky Derby hats are all about character, femininity and tradition—basically the bigger, the better.  Believed to bring the wearer good luck, this long-established practice has taken root from the early days when late 19th and early 20th century women attended the horse races as a way to be seen in the latest fashions, and we carry on that tradition today. Why go to the Derby if you don’t want to show off your glorious new millinery? Ahead we found some of our favorite pieces for a fanciful day at the races—but be warned—these hats are not for the faint of heart. 

kentucky derby hats
Photo Courtesy of Lady Diane Hats

Lady Diane Hats specializes in Kentucky Derby dress hats that are handcrafted works of Victorian art. Sticking closely to traditional styles, there is a surprisingly large selection, but if you don’t see something that strikes your fancy you can send over your ideas and work with them to create your own one-of-a-kind topper. The site also allows you to virtually try on a hat so you can be sure it’s going to look great for Derby day. We love the Triple Crown, one of the most elaborate and feathery pieces we’ve seen so far. Available at Lady Diane Hats and priced at $1,150.

kentucky derby hats
Photo Courtesy of Maggie Mae Designs

My earliest memory of horse racing was seeing Audrey Hepburn impeccably dressed from head-to-toe as Eliza Doolittle in My Fair Lady. What left an impact wasn’t the stoic choir of spectators, nor her cockney screams for the horse to “move your bloomin’ ass!” but rather her pristine lady-like outfit. Designer Maggie Mae at Maggie Mae Designs creates millinery that emulates Doolittle’s beautiful perfection with custom designs and a selection of hats that will undoubtedly make you feel much like a sophisticated Hepburn. Our favorite is the Kristy-Der—a silk hat decorated with black satin, silk organza and a pink taffeta rose. Available at Maggie Mae and priced at $828.

kentucky derby hats
Photo Courtesy of Hat-A-Tude

While taller, puffier hats seem to get most of the attention, toppers that are a little more down to earth can be just as extravagant. Hat-A-Tude offers simpler pieces with just as much style and personality as some of their gaudier counterparts. Hats are made upon purchase and can be customized with brim length and size adjustments when needed. The Ivory & Fuchsia Moss Rose hat is easily our favorite in their collection and their most popular style. Available in a five or six inch brim, this topper features ivory grosgrain ribbon and a handmade 12-inch, sheer, organza rose in ivory, fuchsia and green. Plus with a style this simple we can wear it to our next garden party. Available at Hat-A-Tude and priced at $190.

kentucky derby hats
Photo Courtesy of Hats In The Belfrey

If the size of your hat decides your luck on the day of the races, Christine A Moore’s designs pretty much guarantee a win. Her collection of ginormous toppers are handmade in New York City and include styles that range from petite fascinators to our favorite—the Clara Panama Big Brim. Made from finely woven Panama straw and a simple, lace-striped bow, what this hat lacks in ornaments it makes up for in size. While it won’t be the loudest hat at the Kentucky Derby it will certainly be the largest; it’s understated and still eye-catching—just not too much. Available at Hats In The Belfrey and priced at $490.

kentucky derby hats
Photo Courtesy of Hats and Veils

If there was a celebrity of the millinery world, Polly Singer would be it. Having designed hats since 1993, Singer has designed toppers for celebrities, Hollywood movies like Austin Powers and Speed 2, and many of her creations end up in the Winner’s Circle of the Kentucky Derby. Each piece is hand sewn and made to the specifications of each client for a truly couture experience. We love the Azure, a gorgeous, baby-blue piece inspired by La Cote d’Azur, and topped with silk organza flowers, ivory feathers and parasisal straw. Available at Hats and Veils and priced at $410.

Marissa Stempien

Marissa Stempien graduated with a degree in English Literature and a minor in Asian Studies from San Francisco State University. Previously a beauty editor, Marissa now utilizes her love and passion of luxurious fashion everyday as Fashion Editor of JustLuxe. Originally from Santa Barbara, CA, Marissa has traveled to various cities across the globe, most recently returning from living abroad...(Read More)

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