15 Hats and Looks From The Kentucky Derby That Could Be Worn to Church - Page 2

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The Kentucky Derby’s iconic hat tradition is a story woven from European influences and local flair. The roots reach back to the racetracks of England and France, where elaborate hats and refined fashion were as much a part of the spectacle as the horses themselves. When Colonel Meriwether Lewis Clark Jr. and his wife Mary founded the Kentucky Derby in 1875, they brought that sense of style home to Louisville. Mary Clark, a fashion influencer ahead of her time, famously rode through town in an elegant carriage, encouraging locals to don their finest attire—including hats—for the new racing event.

From that first Derby onward, hats became a mark of celebration. What started as a borrowed custom soon evolved into an unspoken tradition. Today, sporting a hat at the Derby isn’t just about style; many consider it a token of good fortune. The larger and more extravagant the hat, the bigger the luck, or so the saying goes. The Kentucky Derby Museum now showcases a kaleidoscope of historic hats that have graced the stands, each piece telling its own sartorial story.

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Fascinators, those playful and often feathered headpieces, have also found their place at the Oaks, the spirited companion event to Derby day—but whether you opt for a subtle fascinator or an exuberant brimmed statement, your headwear is sure to turn heads.

This year’s gallery captures the creativity and color worn by stars like Simone Biles, Jonathan Owens, Star Jones, Joey Fatone, Tyrese Maxey, and more. Their looks blend high fashion with Derby tradition, making each ensemble fitting for The Kentucky Derby and Sunday service at church.

From the very first parade of hats to the dazzling displays of 2025, Derby headwear offers a chance for personal expression, celebration, and maybe even a little luck on race day.

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The article ‘15 Hats and Looks From The Kentucky Derby That Could Be Worn to Church‘ was created with the help of Jasper.AI

1. Guests attend Kentucky Derby 151 at Churchill Downs

Guests attend Kentucky Derby 151 at Churchill Downs wearing big hats topped with feathers and flowers

2. A woman attends Kentucky Derby 151 at Churchill Downs

A woman attends Kentucky Derby 151 at Churchill Downs wearing a pink straw hat with a flower and a ruffled brim

3. Star Jones attends Kentucky Derby 151 at Churchill Downs

Star Jones attends Kentucky Derby 151 at Churchill Downs wearing a white dress with a blue and white hat decorated with pastel tulle and feathers

4. A woman attends Kentucky Derby 151 at Churchill Downs

A woman attends Kentucky Derby 151 at Churchill Downs wearing a royal blue facinator with swiss dots and a flower

5. Izabel Araujo and Joey Fatone attend Kentucky Derby 151 at Churchill Downs

Izabel Araujo and Joey Fatone attend Kentucky Derby 151 at Churchill Downs in coordinated their blue and white floral outfits with matching hats

6. A woman attends Kentucky Derby 151 at Churchill Downs

A woman attends Kentucky Derby 151 at Churchill Downs in a large mint green hat topped with a white rose and pink ribbon. 

7. Jonathan Owens and Simone Biles attend Kentucky Derby 151 at Churchill Downs

Jonathan Owens and Simone Biles attend Kentucky Derby 151 at Churchill Downs coordinated matching lavender and white outfits with matching hats

8. Carmelo Anthony attends Kentucky Derby 151 at Churchill Downs

Carmelo Anthony attends Kentucky Derby 151 at Churchill Downs wearing a monochromatic sage green suit with a newsboy cap.

9. A woman attends Kentucky Derby 151 at Churchill Downs

A woman attends Kentucky Derby 151 at Churchill Downs wearing a wide brim straw white hat with bright flowers.

10. Warren Moon attends Kentucky Derby 151 at Churchill Downs

Warren Moon attends Kentucky Derby 151 at Churchill Downs  in a traditional silver suit with a cream fedora 

11. A woman attends Kentucky Derby 151 at Churchill Downs

A woman attends Kentucky Derby 151 at Churchill Downs in a wide-brimmed mesh fuchsia hat with big flowers

12. Tyrese Maxey and Lavender Briggs attend Kentucky Derby 151 at Churchill Downs

Tyrese Maxey and Lavender Briggs attend Kentucky Derby 151 at Churchill Downs wearing pinstripe and florals with a cream colored facinator. 

13. A woman attends Kentucky Derby 151 at Churchill Downs

A woman attends Kentucky Derby 151 at Churchill Downs wearing a peach straw hat with pastel flowers 

14. Eden Bridgeman Sklenar attends Kentucky Derby 151 at Churchill Downs

Eden Bridgeman Sklenar attends Kentucky Derby 151 at Churchill Downs in a mint green cascading dress with a feathered hat and veil.

15. A woman attends Kentucky Derby 151 at Churchill Downs

A woman attends Kentucky Derby 151 at Churchill Downs in a black and white hat flourishing with ostrich feathers.