Putting together a Kentucky Derby outfit can feel like a sport of its own — and an expensive one at that. First‑timers are often stunned to learn that a custom Kentucky Derby hat can easily top $500.

The Kentucky Derby returns on Saturday, May 2, and as much as we love the thrill of the annual horse race, our hearts are firmly set on curating the perfect Derby‑day look. While dramatic hats and ...

From statement hats to standout suits, a Kentucky Derby outfit is all about dressing like you mean it, and this year’s Derby fashion trends are off to the races. TODAY style correspondent Zanna ...

Of all the fashion events of the year, the Kentucky Derby is in a league of its own. The horses may be the main event on the track, but in the stands, it's all about the dresses. Basically, if there ...

"I start in January looking for a dress that is long enough that I can wear fleece leggings underneath in case it's chilly like today and the dress has to have pockets so I can use them as handwarmers ...

Add Yahoo as a preferred source to see more of our stories on Google. Fans will flock to Churchill Downs in Louisville on Saturday for the 2025 edition of the Kentucky Derby. The Derby is the most ...

Head-turning hats, bold, bright dresses, chic shoes and accessories were the basic elements of the well-dressed during the Kentucky Derby 2025.

If you had to guess which former NFL star would get called out for their outfit at the Kentucky Derby in 2026, Rob Gronkowski would probably come close to the top of the list, right? Gronkowski was a ...

Cooler temperatures at the 2026 Kentucky Derby prompted attendees to creatively layer their outfits. Veteran racegoers prioritize practical yet glamorous attire, often planning for unpredictable ...

We're set for the 2026 Kentucky Derby on Saturday, but if you're attending the race at Churchill Downs, there's a dress code.

Fans will flock to Churchill Downs in Louisville on Saturday for the 2025 edition of the Kentucky Derby. The Derby is the most prestigious event in horse racing, headlining the Triple Crown, and if ...