First Daughter Outfits That Totally Missed The Mark

Few are ever prepared to become a first daughter. It's an odd job to take on, and you probably didn't ask to be a member of the closest thing the United States has to a royal family. And yet, the world is watching everything you do, listening to everything you say, and judging how you act in the public eye for four to eight years. Many former first daughters have shared how living under a microscope during a time when everyone wants to know about their family can be hard to come back from when a new family moves in. The pressure has made several of them act inappropriately, though they were well aware of the potential chatter they'd receive.

Because many inquiring minds surround first daughters, it should come as no surprise that a first daughter's clothes are also subject to discussion, mockery, or ridicule. Despite their access to any clothing brand or designer they desire, some first daughters just can't help but make the wrong style choices, even when they're guaranteed to be photographed. Over the years, many first daughters have worn outfits that completely missed the mark, reminding us that money doesn't buy you class ... or good taste. Here are some first-daughter looks that should've stayed in their closets.

Another Trump-style error came courtesy of Tiffany Trump, Donald Trump's daughter with his second wife, Marla Maples. As one of the younger members of the Trump family, she likely doesn't remember a time when her family's name wasn't in the spotlight. However, in 2016, she became a first daughter for the first time. Due to her young age, it made sense that she didn't dress the part. However, that didn't mean she got a pass for her election night fashion faux pas, which totally missed the mark and embarrassed her already controversial family.

The night of her father's first election to the presidency, Tiffany Trump wore a short blue shiny dress as she appeared onstage with Donald, his current wife, Melania Trump, and the rest of his children. The outfit was wrong for various reasons. For starters, Tiffany Trump's decision to wear a shorter dress than the rest of her female family members was instantly noticeable and caused the wrong kind of attention. It looked as if she had somewhere more fun or important to be and didn't put much effort into getting ready for the massive event.

Chelsea Clinton's time as a first daughter wasn't the easiest. Her father, Bill Clinton, the 42nd President of the United States, was involved in one of the most infamous political scandals in U.S. history. For those unaware, it involved President Clinton, Monica Lewinsky, a quote heard 'round the world, and a notorious blouse. And yet, somehow, Chelsea Clinton has only made a few public faux pas, one of which came with an odd fashion choice.

In 2023, Clinton attended Gov. Wes Moore's inauguration ceremony looking like she got dressed in the dark. When she arrived, she was spotted wearing two different black shoes, one with a round-toed heel and another with a pointed heel. The mishap was quite embarrassing, which Clinton acknowledged in an X (formerly Twitter) post she shared soon after the ordeal. In the post, she added that Oprah Winfrey was the one who told her she had two different shoes on, making the mistake even more shameful. "Getting ready early this morning to head to Annapolis for ⁦@iamwesmoore⁩'s inauguration, I grabbed two black heels, and failed to grab an actual pair of shoes," Clinton explained. "I didn't notice until I was in Penn Station. ⁦@Oprah⁩ of course noticed as soon as I sat down next to her...!"

Although a first daughter isn't explicitly expected to make a name for herself outside of the first family, several have gone on to thrive in spaces away from their presidential fathers' names. Jenna Bush Hager is definitely in that category, making her mark as a journalist soon after her father, President George H.W. Bush's presidency ended in 2008. She rose as a writer and an editor-at-large for Southern Living magazine and eventually found her footing in the morning news space. In August 2009, Bush Hager made her debut as a correspondent and contributor on the "Today" show. In 2024, Bush Hager took over her and Hoda Kotb's "Hoda & Jenna" segment to lead "Jenna & Sheinelle" with her "Today" co-host, Sheinelle Jones.

Her time as a correspondent has earned her a more positive reputation than she had when she and her fraternal twin, Barbara, were known for their party girl days. Still, Bush Hager's rebrand didn't make her a fashionista by any means. One of her fashion flops happened in 2024 as she and Kotb celebrated five years of working together on their show. During their visit to the Empire State Building, Bush Hager wore a Barbie pink two-piece skirt set with cowboy boots. Although there's nothing inherently wrong with wearing a skirt set with boots, this style of boot didn't enhance her outfit at all.

Lara Trump, President Donald Trump's daughter-in-law and the wife of Eric Trump, may only be a first daughter by marriage, but her fashion no-nos are no less impossible to ignore. On February 19, 2023, Trump posed with a group of friends for an Instagram photo shoot that definitely should've stayed in their group chat. The photo included her and her friends wearing "Make America Florida" T-shirts, camouflage leggings, and sunglasses. Most of the women, with the exception of her friend on the far right, also had rifles in their hands, with Trump carrying the largest one as she posed. 

The outfit and photo op were tone deaf, considering the post came as multiple fatal mass shootings occurred across the U.S. Trump's outfit was immediately deemed "shameful" by social media commenters. "SHAMEFUL....tell the mothers who just lost their child from another mass shooting in Tennessee why you think this is ok?" one irate commenter asked underneath the post. "They will never be able to say goodnight to their babies because an assault rifle killed them. Wake up mothers and care about life especially the lives of children. I weep for you and your behavior."

Ivanka Trump is both a first daughter and one of the most prominent faces associated with her father, President Donald Trump's business practices. From her time on "The Apprentice" to her time serving as his senior advisor during his first presidency from 2017 until 2021, she has supported her family's right-wing political stance on multiple issues. In January 2017, this became more apparent on a date night with her husband, Jared Kushner. In the photo, posted on Trump's Instagram account, the couple attended the Actor Awards (formerly the SAG Awards), and Trump wore a metallic dress with a matching silver coin purse. 

While her dress choice was attention-grabbing, that wasn't the worst part. The public also scolded Trump for wearing a dress in the first place, stating it was in poor taste. At the time of her post, the U.S. was detaining refugees in airports across the country. The refugees were photographed wearing aluminum foil as blankets. Many felt the first daughter's actions were tone deaf given the state of the world, while others argued she had the right to enjoy a night out with her husband amid the political unrest.

Jenna Bush Hager is a woman of many talents, and it's perfectly fine if styling isn't one of them. After all, fashion is more about how good something looks on a person; it's also about how well the person puts it together. Based on what she wore while leaving a January 2024 taping of "Today," Bush Hager still hasn't mastered choosing her outfits to fit where she's going ... or even for the correct season. While she appeared to be pleased with her look, she definitely could've done better. The outfit was a sleeveless patterned top with a black short skirt and combat boots. 

The look was inappropriate and made Bush Hager appear as if she hadn't listened to her colleague Al Roker's forecast that week. Although many have seen Jenna go sleeveless in icy temperatures before, this particular look was just plain confusing during the frigid New York City weather. However, because Bush Hager didn't wear a coat outside, we're guessing she didn't mind. The confusing outfit was one of the many times she stepped outside without a stylist, and she told InStyle in 2024 that she takes full credit for all of her on-air looks, good or bad. "It's hilarious because sometimes people will say, 'Fire your stylists,'" she shares. "I think people think because we work on television that I have a stylist and I have to say, 'I would be firing myself.'"

Malia and Sasha Obama were both in elementary school during their father President Barack Obama's presidential campaign and his two-term presidency, and they were 10 and 7, respectively, at the time of their dad's 2008 presidential win. Over the years, we watched them blossom into adolescence, most of which took place during their time in the White House. After President Obama's term ended in 2016, Sasha and Malia continued showing the world they were all grown up and living life their way, even if billions of eyes were on them.

The first inkling of this was when they were both spotted smoking cigarettes. Additionally, the sisters' fashion sense sparked many conversations on social media, including their club attire. In 2021, Page Six spotted Malia and Sasha out at a party hosted by Drake. For the outing, the eldest Obama daughter wore floral leggings with a floral printed lace-front top in photos taken by paparazzi. The outfit could be deemed inappropriate because of how much skin Malia showed. However, we're more concerned with how badly styled this look was — the patterns on the top with the leggings were a fashion risk that just didn't mesh well. As for Sasha, her black corset top and green cargo pants were a hit, though many were surprised to see her abs and cleavage up close.

Tiffany Trump has transformed her style before our very eyes. But before she wore club attire to her father's inauguration, she wore another outfit that totally missed the mark. While attending VH1's Save the Music Benefit in 2015, Trump wore a strapless flesh-colored dress with blue sequins over it, according to the Daily Mail. The dress was more fitting for a cocktail hour than a charity event, though she didn't seem to mind based on the photos taken.

In addition to Trump's look for the night, her behavior that night wasn't quite becoming of a future first daughter. During the event, photographers snapped photos of the University of Pennsylvania graduate in the front row during Derulo's performance and sang along to his songs and posed for selfies with the cast of E!'s short-lived reality show, "Rich Kids of Beverly Hills." Trump's outing was far from what some may expect from someone whose father was on the presidential campaign trail, though it didn't affect President Donald Trump's eventual win.

Meghan McCain's questionable and expensive fashion choices are something that are clearly here to stay. She made it on the inappropriate outfit list again due to her tacky accessory choice during her father's presidential campaign. In 2008, McCain attended a campaign rally on her dad John McCain's behalf at Otterbein University in Westerville, Ohio. The outfit she wore to the rally could've been fine on its own, as she was seen wearing a short-sleeve, knee-length black dress, which she paired with black hose and pumps. She also added multiple curls to her blonde hair, opting for a classic look.

But it was McCain's necklace that threw the look completely off. According to photos obtained by Daily Kos, reported in 2008, she wore a pearl necklace with a pendant featuring a portrait of Abraham Lincoln. Considering that she was supporting her father, whom she hoped would become the 42nd president of the United States, it's quite possible that McCain wore the necklace to pay homage to one of the leaders who came before him. Unfortunately, the necklace drew unwanted attention to her otherwise decent outfit and was a horrific choice on her end.

Jenna Bush Hager made yet another failed attempt at fashion with a dress that was befitting of a lazy Saturday or Sunday at an event where wearing the wrong outfit can haunt you for the rest of your days. In 2019, Bush Hager attended the Council of Fashion Designers of America (CFDA) wearing an outfit that no designer at that event would've wanted to claim. Bush Hager wore a red oversized dress that would've also been a hit during a cozy night on the couch. The massive, Snuggie-like gown did nothing for her figure, which it buried. 

What's even worse is that Bush Hager seemed to enjoy the look she chose for the night. While on the red carpet, she accessorized the look with silver shoes and a matching handbag. However, though the accessories enhanced the outfit, the dress itself wasn't what anyone would expect from someone of Bush Hager's status, which seems to be a recurring theme with her wardrobe. Though the outfit was wrong, the daytime host's personal life might have had something to do with why she wore a tent-looking dress to one of fashion's biggest nights. During the time of her event, Bush Hager was pregnant with her and her husband, Henry Chase Hager's son, Henry "Hal" Hager.

While the Obama sisters have always been fodder for public scrutiny, it didn't stop them from continuing to make risqué fashion choices, at least not Sasha Obama. However, one of her style choices was so inappropriate that some were hoping she had been cloned. In December 2020, the then-19-year-old University of Michigan student snapped a photo while wearing an airbrushed crop top and pink bikini bottoms, the latter of which was barely covered by a cream-colored sarong. The outfit choice revealed her stomach, which was decorated with waist beads.

The photo, obtained by MEFeater Magazine, sparked multiple online debates. Some wondered if the person posing for the camera was actually Obama or a possible doppelganger. The photo looked a lot like Obama, but due to what she had on that night, some wanted to believe the former first daughter would never be photographed in something so scant. As of this writing, it hasn't been officially confirmed by Obama or her camp that she's in the picture. However, fans further speculated it was her because she wore the same necklace seen in the photo when The Daily Mail obtained a video of her lip-syncing the lyrics to Moneybagg Yo's crude song "Said Sum," which also features the rap duo City Girls, alongside an unnamed friend. As one can imagine, Obama's musical moment was also quite the scandal.