Best Hats for the Kentucky Derby in 2025

While discussing the history of American women’s hats, designer and writer Steven Stolman recalls Stephen Sondheim’s “company”, in which Joanne Wryly asked, “Is anyone still wearing a hat?”
Hats come and go in a female way, but you can always find a place. Mr. Stolman knew very well. He helped the state's first lady, Beshear, prepares for the 151st run of Kentucky Derby in Kentucky Derby, wearing a dress he designed and a hat he helped choose.
No American sporting event can match the brilliance of the Derby's clothing, and Mr. Stolman is no stranger to this kind of business, wearing a cap to compete in the Royal Ascot competition in England, having a lot of opinions on creating a good hat (and more on the good hats about obsessed with and well-crafted headdresses).
“I think the whole goal should be that you see a beautiful lady wearing a hat, not a beautiful hat that a lady wears,” he said.
In Mrs. Beshear's case, this means getting Mr. Stolman to pair his pink and white silk chair shirt and skirt with Steven Stolman.
As she looks forward to a series of hats seen in the crowd Saturday at Churchill Downs, Mr. Stolman was frustrated that some women might choose poorly because they no longer have the help of trained Minnel and sales staff.
“Buying hats online is really a risky business because there is no chance to see if it fits,” he said. “The real miller is for the wearer, which is different in the world.”
The heavy rain all day complicated things, but as always, the crowd ran away from extreme to low-key range. Almost every woman (and many men) still manages to wear a hat because some traditions are worth keeping regardless of the weather.