Over the decades, fashion has quickly become just as important as the horse racing at the Kentucky Derby. Once a year, all eyes turn to the Churchill Downs Racetrack to marvel at the speed of the horses and admire the unique outfits spectators put on display. But these outfits are not complete without the beautiful, ornate and lavish hats that adorn the men and women at the racetrack.

Extravagant hats and headpieces have made Derby fashion iconic. In fact, 2018 marks the first year Churchill Downs announced a featured milliner – Christine A. Moore – for the Derby. From simple boater hats to intricate fascinators, celebrities celebrated the work of dedicated milliners and hatters through their outfit choices, and didn’t let the rain change their plans.

Hatalk Laila Ali

Laila Ali

Laila Ali, professional boxer and daughter of late Muhammad Ali, attended her first Kentucky Derby on Saturday. Wearing a ruffled pink dress and black wedges, she topped off her look with a large, black sideways hat. Complete with flower and tulle trimmings, the height and position of the piece gracefully complemented the vertical ruffle of her dress.

Local Louisville milliner, Dee’s, made the piece for Ali. Dee’s has been making hats for Kentucky Derby goers and horse racing fans for years. Offering both men’s and women’s hats, Dee’s produces custom creations made for sunny (or rainy) days at the racetrack.

Hatalk victoria Justice

Victoria Justice

Former Nickelodeon star Victoria Justice combined quirky and sophisticated with her black and white Derby look. Styled by Madison Guest, a black feathered halo hovered above her head, adding an interesting detail to the simple wide brimmed hat she showcased. Her plain white, wide-legged pant suit allowed the hat to take center stage for the occasion.

Hatalk Johnny Weir
Hatalk Johnny Weir

Johnny Weir

American figure skater Johnny Weir was on site at Churchill Downs on Saturday to cover the events for NBC. In true Weir fashion, he stepped out in a white and beige, bling encrusted ensemble. And, because a jeweled kimono was not enough, he completed the look with not one, not two, but three crowns fastened to his head, an allusion to the Triple Crown in horse racing. With each crown a different sparkling style, this headpiece was truly one of a kind.

While Justified seized the gold on the racetrack, these celebrities brought their best fashion game to the stands. Among the thousands of spectators that were at Churchill Downs for the day, no two hats were the same. Each hat was worn to complement a different outfit, highlight a different personality, and praise an age old tradition of high fashion at the races.

About the Author

Maggie Kreienberg - HATalk Blogger

Maggie Kreienberg is a contributing editor at BRIDES Magazine and is currently based in New York City. She graduated from Pennsylvania State University with a degree in public relations in 2019.