CELEBRITY STYLE & FASHION NEWSJenna Bush Hager Roasts Heated Rivalry's Hudson Williams While Discussing Men's Fashion Trends: 'Who Is That Celebrity in a Diaper?'
Jenna Bush Hager called out Hudson Williams' odd fashion choice.
Aug. 31 2026, Updated 5:35 p.m. ET
Jenna Bush Hager shaded Hudson Williams.
The TODAY With Jenna and Sheinelle host roasted the Heated Rivalry star while discussing upcoming fall fashion trends with her co-host, Sheinelle Jones.
The women consulted fashion expert Preston Conrad on the Monday, August 31, episode to tell them all about what's hot in men's fashion
Jenna Bush Hager assumed Hudson Williams was wearing a diaper.
One of the items on Conrad's list of trending pieces was a pair of loafers, which Williams sported on his way to the Met Gala after-party on the first Monday in May 2026.
"Street style is on its way out," he told the women. "We are seeing, and you know I love this, the return of all things prep."
But his stylish leather shoes weren't exactly what caught Bush Hager's attention.
'Who Is That Celebrity in a Diaper?'
Hudson Williams wore a controversial outfit after the Met Gala.
"Saint Laurent debuted this loafer last year that went crazy viral; everyone was wearing it," Conrad explained before showing photos of Williams and Harry Styles in the iconic shoe.
Bush Hager squinted at the image of Williams in a pair of white silk shorts, knee socks and a tuxedo top and could only relate his outfit to one thing.
"Who is that celebrity in a diaper?" she asked innocently, criticizing Williams' casual style. "There was a celebrity in a diaper."
Jones, too, did a double take when she spotted Williams' off-kilter outfit.
"Was that socks and a diaper?" she asked.
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What Did Fans Think?
Sheinelle Jones agreed with Jenna Bush Hager's description of the ensemble.
Even Conrad had to admit that Williams was wearing a "crazy" ensemble, which included that "diaper" he described as "boxer shorts."
"Do you remember the after-party where he wore that crazy boxer short thing?" he asked. "This picture is about the loafers."
Styles, on the other hand, appeared to have styled the trendy shoe much more appropriately in the women's eyes.
Fans online agreed that Williams' late-night style was giving more baby than it was couture.
"NGL… thought it was a diaper," one person wrote under a picture of his ensemble posted to social media at the time.
The internet was more than happy to roast Hudson Williams' sense of style.
"Dare I say born to be a star?" someone joked.
"Your standard 4-year-old forced into Easter clothing who somehow managed to lose his pants halfway through dinner," yet another quipped.
"What is with these ugly diaper-looking shorts I’ve been seeing lately?" a fifth complained.
Fortunately, Williams' controversial shorts were not on Conrad's approved list of up-and-coming trends.
"Everything is getting a little bit of an upgrade for fall," he noted.
