6 First Lady Makeup Fails That Will Have You Cringing

First ladies of the United States typically represent the softer side of the presidency. Tasked with entertaining and making the People's House feel like home, they also promote family-friendly initiatives such as literacy and nutrition. They're not expected to look like glamour queens, but they do have to look put together in public. However, despite the best efforts of personal assistants and designers, sometimes they step out looking less than their best. We can't forget some out-of-date first lady outfits, such as Michelle Obama's tweed inauguration dress and Laura Bush's matronly 2006 Kennedy Center Honors gown. And even when the presidential spouses are impeccably dressed, sometimes their makeup isn't quite up to par.

Take, for instance, the pic above, which shows one of Melania Trump's worst makeup fails yet. As a former model, the first lady certainly knows how to present a polished look, but there are times when she forgets she's not on a photo shoot. Her heavy eyeshadow and liner are both aging and a harsh contrast to her lightened hair, and the obvious contouring on her nose needs to be blended. Hopefully, she'll bring a lighter touch to her palette during her second go-round on the job. Other first ladies fell victim to their era's style trends, or forgot to check a mirror before facing the cameras. We found some of the more embarrassing examples — ones the FLOTUSes would probably rather not remember. 

As the first lady of Arkansas, Hillary Rodham Clinton got plenty of practice making appearances with her husband. She was perfectly in step with the time; unfortunately, however, that time was the early '90s, when the previous decade's biggest trends were still in vogue. Who could forget the neon eyeshadows, splashy blush, bushy brows, and bright pink lipstick on every magazine cover? ('Fess up — you still have a teal powder buried at the bottom of your makeup case, don't you?) Clinton was right in style when this 1991 photo was taken, but her grandchildren might have a good giggle over their grandma's overdone looks. These days she keeps her palette much more neutral, tending toward beige and brown tones which are far more flattering and suited to a former secretary of state.

Nancy Davis Reagan was quite the stunner back in her Hollywood days, and she strove to maintain her glamorous image as first lady and in her post-presidential years. Like all of us, though, she did have her occasional missteps. In 2007, Reagan attended the Saks Fifth Avenue and Colleagues Annual Spring Luncheon at the Beverly Wilshire Hotel, where she gave a speech in praise of the guest of honor, Brooke Shields. She turned out in a smart tweed suit, but her attempt to match the vermilion shade to her blush and lipstick was just too garish. Reagan's exaggerated eyeliner didn't do her any favors, either. With all due respect, she should have just said no to this look.

They say everything is bigger in Texas, and Barbara Bush was out to prove it in this undated picture from the Republican National Convention. Her signature three-strand pearl necklace had beads visible from space, and her hair was proudly poufed up. But her statement lipstick made too much of a statement. The bright red shade made her teeth look discolored and was too harsh compared to the rest of her face. But as FLOTUS, Bush was everyone's sweet, dog-loving grandma, and as such could be forgiven for a makeup misstep.

Dr. Jill Biden was always more at home in the classroom than in the White House. During her husband's administration, she favored the classic suits of an educator, going glam only for state occasions and other special events. Here, at a 2023 event honoring Australian Prime Minister Anthony Albanese, Biden wore a stunning sheer gown with silver appliqué detailing, putting her hair in a rare but flattering updo. But her uneven foundation, unfortunately, gave her a raccoon-eye effect, and it was just a shade too dark, calling to mind Donald Trump's makeup fails in which he used a heavy hand on the orange base.

Laura Bush has the distinction of being only the second first lady to be the wife of one president and daughter-in-law of another. (Louisa Catherine Adams, wife of John Quincy Adams, was the first.) She was well-known and respected for her literacy initiatives, and in her post-White House years, she became an author herself. Here, she's seen at a book signing for her memoir, "Spoken From the Heart." But if we're being honest, Laura's heavy matte foundation is more of a distraction than an enhancement. And like mom-in-law Barbara Bush, she chose a bright red lipstick that clashes with the subtler tones of her blush and liner, not to mention risking an embarrassing tooth smudge. (Do we spy a hint of one here?)