Why do Kentucky Derby attendees wear hats?
Because it was the early 1900s and hats were part of the fashion, they also became part of the ongoing tradition. The hats only grew more wild and fanciful when the Kentucky Derby became widely televised in the ’50s and ’60s — naturally, attendees wanted a shot at standing out from the crowd.
Iconic Hats to Serve as Inspiration
The Kentucky Derby hat tradition continues today — and whether you plan on attending in person or will watch the races from the comfort of your own living room, wearing a hat makes any event (but particularly this one) more fun. The world of headwear is a vast one, so check out these iconic lids to serve as your inspiration. Whether you want something whimsical (like a fascinator), or a something a little more understated (like a fedora), there’s truly a hat out there for everyone.
Go Royal In a Fascinator (and Don’t Muss Your Hair)
The fascinator, with its classic bows, varied decorations, and vibrant colors, seems aptly named. It’s the kind of headwear that would make anyone take a second glance — just look at Princess Kate Middleton’s pale yellow fascinator above. But according to some fashion experts, fascinators aren’t really hats at all. They’re actually small, decorative headpieces, typically attached to the head with pins, that are worn to formal events like church services and weddings, and famously worn by royalty, as far back as Marie Antoinette in the 17th century.
Stand Out from the Crowd In a Bold Bowler
Looking for another classic option with a little more coverage? Opt for a bowler hat. And before you worry about bowlers being more of a menswear thing, opt for a feminine, whimsical one like the purple stunner above. Its rounded top and narrow brim make it an understated but elegant choice. History of Hats notes that the bowler was invented in 1849 by British politician and soldier Edward Coke. He had it made for the people who worked on his estate, so that they wouldn’t hurt their heads on low-hanging branches while on a horse. The low, hard top of the bowler protected heads while still looking fashionable. And though it started as menswear, it’s now beloved by many women, namely Diane Keaton. Her Annie Hall bowler is iconic, and she’s made it her signature look throughout the years. Check out this Instagram video in which Keaton gives a tour of her extensive hat collection, many of which are bowlers.
Wear Your Whimsy In Colorful Organza
One of the most popular hat choices at the Kentucky Derby is the organza hat. Don’t the two colorful, frilly organza hats above just make you want to say something charmingly Southern, like “bless your heart?” Organza, originally made from silk, is now also composed of synthetic fabrics, like nylon and polyester. It’s sheer and breathable, making it the perfect material for keeping you cool in the warm Kentucky springtime sun. And because organza is so lightweight, hats made with the stuff can be loaded with frills, flowers, beads, bows — most any decorative element your heart desires — without making the wearer feel over-encumbered.
Summon Mystery in a Vintage Cloche
If Derby day will still be a little chilly in your neck of the woods, consider the fashionable and form-fitting cloche hat, like this vibrant cherry-red one that’s sure to turn heads. Created in the early 1900s, the cloche didn’t become a symbol in the fashion realm until the ’20s, when it became synonymous with flappers and the Jazz Age. With their small brims and deep tops, it makes sense that their name comes from the French word for “bell.” They’re still a popular topper today: Aretha Franklin’s silver-bowed cloche that she wore to Barack Obama’s Inauguration in 2009 made waves — and for good reason. It’s sophisticated and still stands out, the perfect combo for the Kentucky Derby.
Celebrate Tradition In a Classic Straw Hat
If April showers brought you May flowers and warm sunshine, a straw hat is a beautiful, breezy choice for Derby day. Straw hats aren’t just beach day essentials. They’re timeless and easy to make casual or formal — just like this ornate, floral, snow-white number. There are many shapes, sizes, and colors of straw hats, but they all have one thing in common: They’re light and comfortable. Originally worn for sun protection in 15th century Asia, they became more of a fashion statement in Europe in the 1700s and 1800s. Straw hats experienced a boom in popularity stateside when President Theodore Roosevelt was photographed wearing one on a trip to the Panama Canal in 1906. With their perfect blend of utility and fashion, straw hats have secured a timeless place in the fashion world. One of our favorites? Julia Roberts’ crisp white straw hat that she wore to the polo game in Pretty Woman. Not considering a classy straw sunhat would be a big mistake — huge!
Strike a Power Pose in a Feminine Fedora
Before you worry that we’re telling you to dress up like Indiana Jones for the Kentucky Derby, keep in mind that there’s more than one kind of fedora. Take, for example, the ultra-girly hot pink fedora above, bedecked with a veil and flowers. Popularized by and named after a French play in late 1880s, the fedora was seen as a womenswear staple with masculine vibes. It remained a mainstay in the fashion realm worldwide, often becoming associated with mystery, and a blend of ruggedness and refinement. One of our favorite fedora moments is Judy Garland singing “Get Happy” in the 1950 movie Summer Stock. Watch the video below — we apologize in advance for you having this stuck in your head all day!
Make Like Meghan in a Sophisticated Pill Box
Pillbox hats are synonymous with classy ’60s flair. Meghan Markle’s cream pillbox hat above is minimal in design, but glam enough to make a statement. The low, brimless hat, named for its similarity to the boxes in which pills were once sold, was made popular in America by none other than Jackie O. She wore a pillbox hat to the inauguration of her husband, John F. Kennedy, in 1961. In a 1966 interview with the hat’s maker, Roy Halston Fenwick said that he accidentally made the hat a little too small for her — and when a gust of wind threatened to blow it off, she dented it in attempting to keep it from flying away. Women wanted their pillbox hats to look exactly like Jackie O’s, forcing hat makers to produce pillboxes with identical, small dents in the top. Talk about a trendsetter!
Ready for the races? Any of these hats will make you feel like you took first place. Now whip up a mint julep and enjoy!