ENTERTAINMENTJenna Bush Hager Reveals Why She Turned Anna Wintour Down for Drinks: 'I Felt Weird'

On 'TODAY With Jenna & Friends,' Jenna Bush Hager admitted she avoided grabbing drinks with Anna Wintour.
Dec. 11 2025, Published 4:19 p.m. ET
Jenna Bush Hager was shy when offered to hang out with one of the most powerful names in fashion.
During the Thursday, December 11, episode of TODAY With Jenna & Friends, the media personality, 44, revealed that she couldn’t muster the confidence to join longtime Vogue editor Anna Wintour for drinks.
Bush Hager and guest co-host Brooke Shields were discussing the recently-announced Met Gala chairs when she recalled an awkward moment with the longtime Vogue editor.
Brooke Shields guest-starred on 'TODAY With Jenna & Friends.'
“One of the years [I went to the Met Gala], somebody who worked for Anna Wintour came out, who I know, and was like, ‘Anna wants you to come in for drinks,’” she remembered. “I was like, ‘No way. Me? I’m just working here on the stairs.’ I felt weird. It was lovely, and I wish I had. There’s some moments…I’m confident, but…one word I want to say but can’t…the balls. Sorry, I had to say it.”
She continued, “I wish I had it to say, ‘Okay, I’m going to come in.’”
Shields reassured the host that there will be “plenty of other opportunities” to redeem herself.
Jenna Bush Hager Attended the Met Gala in the Past

Jenna Bush Hager was intimidated by Anna Wintour.
Bush Hager walked the famous steps of the Met Gala in the past. In 2018, she stunned in a long-sleeved, red lace gown that retails for $3,995 by Lela Rose. She sported matching smoky red eyeshadow and tousled blonde locks. In 2017, she stood behind the camera as a correspondent for Today, interviewing celebrity guests on the carpet.
Brooke Shields' Met Gala History
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Both Jenna Bush Hager and Brooke Shields have attended the Met Gala.
During Thursday’s episode of Jenna & Friends, Shields, 60, reflected on her own Met Gala experience.
“The first time I ever went to the Met Gala was 1983,” she recalled as images of her past outfits flashed on the screen.
One year, she donned a Calvin Klein dress because she had to gift a pair of jeans she wore by the designer to the Metropolitan Museum of Art.
“As one does…it’s really ridiculous,” the actress joked. “A pair of my jeans are in the Met….they posed the mannequin in the model pose I was in, and the hair was all matted and weird. It was very odd to walk through and see me, but it was an honor.”

Brooke Shields contributed a pair of jeans to the Met.
Shields admitted that she still has two pairs of the jeans, one that has been hanging on a hook for years. However, when she went to search for the garment yesterday, she couldn’t find it.
“They’ll show up,” she insisted. “My house is like a black hole, so they will show up.”

Brooke Shields told Jenna Bush Hager there would be 'plenty of other opportunities' with Anna Wintour.
The Pretty Baby alum still holds onto the clothing because her mother is sentimental.
“She took the jeans practically off my body!” Shields exclaimed. “She was like, ‘Trust me. One day.’”


