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When discussing the history of women’s hats in the United States, the designer and author Steven Stolman was reminded of Stephen Sondheim’s “Company,” in which Joanne wryly asks, “Does anyone still wear a hat?”Hats come and go in women’s fashion, but there is one place you can always find them. Mr. Stolman is well aware of that. He was in Kentucky to help Britainy Beshear, the first lady of the state, get ready for the 151st running of the Kentucky Derby, which she was attending in a dress he designed and a hat he helped select.No American sporting event can match the sartorial splendor of the Derby, and Mr. Stolman, who is no stranger to such affairs, having donned a top hat to attend Britain’s Royal Ascot races, had many opinions on what made a good hat (and many more on fascinators and elaborate headdresses being entirely separate things).“I think that the whole goal should be that you see a beautiful lady wearing a hat,” he said, “rather than a beautiful hat being worn by a lady.”Britainy Beshear, the first lady of Kentucky, worked with the designer Steven Stolman on her outfit for the Derby.David Kasnic for The New York TimesIn Mrs. Beshear’s case, that meant having Mr. Stolman pair a pink-and-white silk check shirt and skirt from his Steven Stolman for J. McLaughlin collection with a hand-blocked white sinamay hat by Gigi Burris that was trimmed with twisted goose feathers.When looking ahead to the array of hats that would be seen in the crowd on Saturday at Churchill Downs, Mr. Stolman expressed some dismay that more than a few women were likely to choose poorly as they no longer had the help of trained milliners and sales people when shopping.“Buying a hat online is really risky business because there’s no opportunity to see if it even fits,” he said, adding that “genuine millinery is made to fit the wearer, and that makes all the difference in the world.”Heavy rain throughout the day complicated things, but the crowd of 147,406, as always, ran the gamut from extreme to understated. And nearly every woman (and plenty of men) still managed to wear a hat, because some traditions are worth keeping, regardless of the weather.In Lori Walker’s case, the rain on Saturday created a fun effect on her hat. David Kasnic for The New York TimesIndra Mumba’s sunglasses went so well with her outfit that she kept them on despite the dreary day.David Kasnic for The New York TimesCathy Shannon was among the attendees who took a break from the weather by finding a dry place inside.David Kasnic for The New York TimesJim Oehmcke’s white shirt and hat made his accessories pop.David Kasnic for The New York TimesCarrie and Jeff Ketterman did not let the weather get in the way of their spectacular ensembles. David Kasnic for The New York TimesAs the day went on, the party atmosphere managed to come through.David Kasnic for The New York TimesRonnie McCraven went with a loud outfit and an understated hat.David Kasnic for The New York TimesA rainbow of feathers would stand out in any crowd, but a dreary day made it pop even more.David Kasnic for The New York TimesSome hats blurred the line between hats and dioramas. David Kasnic for The New York TimesButter yellow is a color of the moment, and this group was ready for that moment.David Kasnic for The New York TimesA large splash of red in a black and white outfit made for a striking look.David Kasnic for The New York TimesCheryl Hamilton-Hill leaned in on the rain and added a yellow rain coat to her outfit.David Kasnic for The New York TimesA hat this large made you want to see the dress that went with it. David Kasnic for The New York TimesBruce Asmussen’s Pabst Blue Ribbon hat was as creative as they come.David Kasnic for The New York TimesThe people who went out to their seats did so in ponchos, with some covering their hats as well.David Kasnic for The New York TimesAlbert Smith and Julie Nickel coordinated their outfits nicely. David Kasnic for The New York TimesSome rain coats blended more seamlessly than others.David Kasnic for The New York TimesSvetlana Mumba stood out in pink.David Kasnic for The New York TimesFascinators, fedoras and baseball hats could all be found at Churchill Downs.David Kasnic for The New York TimesA clear raincoat was as unobtrusive as possible, though some people chose to just get rained on.David Kasnic for The New York TimesJoe Rogers and his daughter, Talea, made some adjustments outside Churchill Downs.David Kasnic for The New York TimesAmelia Hauschild stayed dry under an overhang with her husband, Martin Garcia.David Kasnic for The New York TimesThe weather may have been lousy, but Katherine Darius managed to let a smile sneak through while standing under a tree. David Kasnic for The New York TimesThe weather left a well-dressed crowd a bit water-logged, with dreams of nicer weather next year.David Kasnic for The New York Times More