Perhaps in hindsight, the American flag shirt was a little much.
TODAY's Jenna Bush Hager had some fun with Andy Cohen on Nov. 29 when she gave her take on old family photos with former President George W. Bush and first lady Laura Bush in an episode of "Watch What Happens Live."
One of the photos featured Jenna, 41, and her twin sister, Barbara, as 8-year-olds wearing some, uh, very patriotic matching shirts featuring stars and stripes.
"If you look closely, Barbara and I both have a little patch for fanny packs that hook onto that. I’m not sure why," Jenna told Cohen. "I’m not sure why (my mother) felt we should dress like that."
Jenna then reflected on a quintessential teen-style fail from 1995 in a photo from her father's nomination for governor of Texas. She's shown sitting next to her grandparents, former President George H.W. Bush and first lady Barbara Bush, who is giving her a wide-eyed look.
Jenna's dark hair in the photo was inspired by the iconic '90s television character played by Claire Danes.
"I had dyed my hair to look like Angela Chase in ‘My So-Called Life,'" Jenna said. "I just used food coloring. I’m sure my parents were so proud of me."
"It looks like Grandma Barbara’s like (nope face)," Cohen said.
In a photo from George W. Bush's inaugural ball in 2001, Jenna shares a happy moment with her father in which she's also trying to defuse a wardrobe malfunction.
"It’s really sweet, but if you notice, my hand is going like this," she says, gesturing near her chest. "My dress fell off."
She also spoke with Hoda Kotb on TODAY in 2017 about the near disaster in full view of the cameras at that celebration.
"My dad spun me, and my dress nearly fell down," she said. "In that moment, I’m thinking, ‘Ohhhhhh, no.’’’
Jenna also shared a photo from her father's second inauguration in 2005, as well as one with Dallas Cowboys owner Jerry Jones from her first broadcast as a member of TODAY in 2009.
"It was the first day that the Cowboys stadium opened and so it was pretty cool," the Texas native said.
Finally, Jenna always gets in the spirit for TODAY's Halloween celebration, and she looked back fondly on her 2014 costume wearing the mom jeans from the classic "Saturday Night Live" skit featuring Rachel Dratch, Tina Fey, Maya Rudolph and Amy Poehler.
"By the way, I love those jeans," Jenna said. "And that was the actual wigs that they wore (in the skit)."