A week or so ago, Britainy Beshear, first lady of Kentucky and the wife of Gov. Andy Beshear, a potential contender for the 2028 Democratic presidential nomination, was standing in the pastel sunroom off her historic, chintz-bedecked parlor in the governor’s mansion, trying on a hat.
Not any hat, of course. It was her Kentucky Derby hat, a cream and navy construction with a wide brim and a spray of raffia flowers. She was trying to situate it over her French twist so it sat at a jaunty angle but didn’t obscure her eyes. It was a complicated balancing act.
But then, for Beshear, so is the whole Derby weekend.
For most people, the Derby is a blast: a mint-julep-fueled mélange of hats and horse racing. But for Beshear, 46, it is also work. As the de facto hostess of the state, she has to welcome guests of all political stripes, representing her husband’s administration as well as Kentucky while presiding over a breakfast, a gala and the presentation of the winner’s trophy — and posing for countless photo ops — in three different outfits over two 12-hour days.
That’s a lot to juggle at any time, but this year, given the attention on her husband, it’s even more complex. You might even say it’s something of an audition.
Few governor’s spouses have a profile beyond their home states. (Had anyone outside Minnesota heard of Gwen Walz before Vice President Kamala Harris chose Gov. Tim Walz to be her running mate? How about Bill Hochul, husband of Gov. Kathy Hochul of New York?) But the Derby is, said John McCarthy, a Democratic strategist who was a senior adviser to President Joseph R. Biden Jr., “one of the most high profile sporting events in the country other than the Super Bowl.”
It’s a day when the eyes of not just the state but also the country are on the Beshears, and that’s an opportunity that, as McCarthy pointed out, “other candidates don’t have.” It’s a chance for the governor to show off his leadership and his personal side — that is, his family. And he gets to do it, said Tammy Haddad, the founder of the Haddad Media consultancy, while schmoozing with voters, donors and other political leaders “on national television.”
Though the first lady is quick to say that the Derby is just about the Derby and presenting the best face of Kentucky to the world, the stakes clearly haven’t escaped her. The Instagram post of the first family on Derby morning, all of them dressed in their finery, is always one of the governor’s most popular of the year. Last year, Britainy Beshear’s Derby hat, a natural hemp number with pink trim, made the pages of Town & Country as well as this newspaper. By September, she and her husband were in Vogue.
Hence the dress rehearsal.
Image as Destiny
It is probably not a coincidence that last year, for the first time since her husband entered politics, Beshear connected with a stylist: Steven Stolman, a designer who had worked at Albert Nipon and Scalamandré and who recently restarted his own line.
And it is telling that when asked about her political fashion role models, Beshear names Michelle Obama, for whom clothes became such a powerful tool that they formed the basis of a book. Beshear is already practiced enough to mention that Gigi Burris, the milliner who made her hat, works with local craftspeople in New York’s garment district. And she knows the philanthropic symbolism of almost the entire color wheel off the top of her head: “Red, women’s heart health. Orange, hunger. Blue, human trafficking awareness.” (Human trafficking has been a focus for Beshear as first lady, and she has worked to raise awareness about what role sporting events like the Derby play in the crime.)
Like the governor’s parlor in the mansion, which has been transformed from sitting room to podcast studio for her husband’s weekly show, the first lady is simply acknowledging the realities of being in office in the social media age, in which image plays an increasingly important role in communication. Little wonder that she is starting to craft her own, one that in many ways reflects the coalition-building promise embodied by her husband, a Democratic governor who has won over a red state not once but three times.
At first glance, Britainy Beshear is very much the model of a certain kind of traditional womanhood. She is platinum blond and thin, and as she says of her style: “I’ve always been more of a conservative dresser. My hemline has never been too short or things been too low.” Rather than the sheath dresses that have become popular in Washington, she favors full skirts under fitted bodices. The effect is sort of Jill Biden meets Fox newscaster.
“I feel like I was born into the wrong fashion decade,” she said. “I should have been born in the ’50s, purely for the clothes, because I love the lines and the cuts.”
At least in her official appearances. In her private life, she tends to wear Uniqlo jeans, an expert half-tuck and Belgian loafers, albeit the Amazon version. (She has two teenagers and a labradoodle called Winnie, and spends a lot of time cheering on the sidelines at her son’s baseball games and her daughter’s riding competitions.)
And in the same way that the governor will wear traditional southern blazers and suits with sneakers — his current favorites say “Dem” on the back of one shoe and “Guv” on the back of the other — she likes chunky or kitten heels, most of them bought on Amazon, rather than stilettos. Either way, her budgets are midrange, rather than luxury. As Stolman put it, the vibe is “more Cinderella than Marie Antoinette.”
Getting Derbied
Beshear has been attending the Derby since 2005, the year before she married Andy Beshear. From 2007 to 2015, she attended as part of the governor’s family, when her father-in-law was in the capitol. She called it her “soft opening.”
By the time she was first lady, she had already made her mistakes and learned what to expect. In 2008, she wore such a large hat that she “couldn’t see anything.” Then there was the year she “looked like a banana,” she said. “I had a yellow fascinator with this massive flower on it with feathers coming out.”
She has learned that when she is crossing the dirt track in fancy shoes, it’s best to “step in somebody else’s footprint or a hoof print so you didn’t sink quite as badly.” That if she has to do a quick change in a car between appointments, it’s advisable, for modesty’s sake, to wear “a tank top and leggings under what you have on.”
“There are times where I need to step it up but only in a way that feels good,” she said. “People can take it or leave it. One of the most liberating things about being in my 40s is that I’m good with who I am and the things I wear, and so no matter how fancy I’m going to be, I’m going to be a fancy me.”
She has also learned the value of a stylist, especially one with his own collection that may be sold online but isn’t well known in Kentucky. “Shopping in Louisville at the main stores means that you will see yourself several times, repeated,” she said, somewhat dryly.
Stolman, who lives between Chicago and California, has worked pro bono with the first lady since 2025. The two bonded over their shared love of midcentury movie-star style and the fact that she grew up in Southern California.
When Stolman described the looks he chose for Derby weekend, he said things like: “It’s very Kay Thompson meets Halston!” and “It’s Katharine Hepburn in ‘Summertime’!” and “It’s Baby Snooks meets Saint Laurent’s Ballets Russes!” (Kay Thompson was the actress who declared “Think pink!” as the imperious magazine editor in “Funny Face.” Baby Snooks was a character created by the comedian Fanny Brice for her early-20th-century radio show.)
The Baby Snooks look turned out to be a raspberry baby-doll taffeta dress Beshear wore for the Oaks (the fillies race on the Friday before the Derby, when guests are encouraged to wear pink for breast cancer awareness); the Hepburn was a sleeveless navy tea dress with white dogwood embroidery and a black tulle petticoat for the Derby itself.
As for the Kay Thompson look, it was a dusty pink T-shirt and lounge trouser set covered in tiny pink sequins that Stolman brought for the gala dinner. Originally, the idea was for Beshear to wear the sequined T-shirt with a big taffeta ball skirt, much like the skirt she had worn to the gala the year before, but Stolman thought she should mix it up a bit.
“I feel like a glitter bomb,” Beshear said when she tried on the sequins. Then Stolman tied a taffeta sash around her waist. “Strangely, I kind of like it,” the first lady mused. Then she practiced sitting down.
“Nothing pokes,” she announced, as though that settled it. “It’s so different from last year,” she said, “Fun without being risky.”
As political spouses go, it could be a motto.
