Jenna Bush Hager's Biggest Makeup Mistakes

Former First Daughter Jenna Bush Hager definitely knows a thing or two about life in the public eye. Bush Hager and her twin sister, Barbara Bush, were 19 years old when their dad, George W. Bush, became the president. Consequently, we've all watched Jenna Bush Hager's stunning transformation through the years. Like anyone, she has tried on different looks and experimented with new styles. And, we have to give credit where credit is due — Bush Hager hasn't had too many egregious makeup fails for someone who has spent so much of her life in the spotlight. Of course, that doesn't mean she hasn't sported the occasional cringeworthy makeup look.

From flattering makeup to stunning makeup-free moments, we've seen Bush Hager pull off different styles over the years. Yet, we've also seen her make some of the same mistakes with her beauty routine over and over again. From a strange love of odd eye shadow placement to an apparent allergy to a good color match with her foundation, there are some horrible habits we'd love to see Bush Hager break in the future of her beauty routine. Until then, though, we've got the biggest makeup mistakes the "Today" star has made over the years.

There's one eye makeup mistake that Jenna Bush Hager seems to make time and time again. It often looks like she has applied an orange-y eye shadow in the space between her eyelid and her eyebrow. This is likely a strategy to contour the upper parts of her lids. In practice, though, she often seems to choose the wrong color and the wrong placement, making the eye shadow appear too obvious and out of place, like she did for an Instagram video in August 2025.

Everyone has a bad makeup day now and then. If there's one time you really need flawless makeup, though, it's when you're in a makeup advertisement. It seems, however, that Jenna Bush Hager doesn't necessarily agree. In April 2025, she shared an ad for IT Cosmetics concealer on Instagram. Between her typical eyeshadow fail, her flat-looking complexion, and her lack of lip product, she didn't set the stage for the concealer well.

Over the years, there's one particular makeup mistake that Jenna Bush Hager has made often: her foundation is a totally wrong color for her. Her makeup look for a Christmas party in 2024 was a prime example of this. One selfie she shared on Instagram, posing with her daughter Mila, showed what looked like a harsh line where her makeup stopped on her neck. Bush Hager clearly needed foundation with a warmer hue, and pairing this mismatched color with other heavy makeup overwhelmed her features.

Another makeup crime Jenna Bush Hager has committed time and time again? We'll call it LOL — lack of lips. During the Hudson River Park Ungala in 2020, Bush Hager pulled the ultimate LOL, wearing a full face of makeup with seemingly no lip product. Over the years, Bush Hager's rare barefaced moments have proven that she doesn't need makeup. Yet, going lipstick-free when the rest of your face is fully covered tends to give off zombie vibes, and this look was a prime example.

When it comes to wearing false eyelashes, size matters. And, just because long, oversized lashes work on one person, that doesn't mean they work for everyone. In Jenna Bush Hager's case, her eyes are small in proportion to the rest of her face. She has tried the occasional eye makeup look that really made her eyes appear bigger and brighter. The makeup she wore in one Instagram video in January 2023, on the other hand, showed how too-big eyelashes can make your eyes look smaller.

In 2012, Jenna Bush Hager arrived at a UNICEF event in a makeup look that was out of the ordinary for her. Bush Hager looked almost makeup-free. Yet, it was clear that she was wearing mascara and eyeliner. Pairing eye makeup with no foundation or lip product made for an odd look that kind of reminded us of when we accidentally fall asleep in our makeup. To make matters worse, Bush Hager seemed to have a bit of a tan on her chest and neck, which made her lack of face makeup more obvious.

Out of all of Jenna Bush Hager's makeup mistakes over the years, heavy, messy eye makeup isn't usually her problem. At a Save The Children benefit in 2013, however, she tried an intense smoky eye look on for size, and well — it definitely didn't work. Not only were Bush Hager's lashes overwhelming for her face, but messy smudging from her heavy eye makeup gave her an asymmetrical look. Evidently, even for an important night out, overly intense eye makeup isn't always a good choice.

It's clear that color-matching her foundation isn't one of Jenna Bush Hager's strong suits. Yet, it's surprising that even when it's time to walk the red carpet, she doesn't always pull out the right foundation shade. Bush Hager looked stunning in deep green at the Golden Globes in 2017. For the most part, her makeup was subtle and pretty, except for one tiny detail. Her foundation looked too light for the rest of her. This was made even more obvious, thanks to all the skin that her off-the-shoulder dress exposed.