10 Tasteless First Lady Looks That Gave Worst-Dressed A New Meaning

Being First Lady of the United States is challenging. Beyond navigating their life as FLOTUS, they are constantly judged and criticized on everything from the strange rules they must follow in the White House to the public appearances and speeches they make, and even what they wear. Can you imagine how exhausting it must be to juggle all of these things and be in the spotlight 365 days of the year? Every move is put under a microscope and every right — or wrong — fashion choice will make headlines. 

With the pressure to balance diplomacy, the transition from their careers (for those who left them behind) to support the president, and serving the general public, looking fabulous while being appropriate for the role is another demanding part of the gig. And not every day can be spot on, with even some of the best dressed first ladies having had their fair share of fashion missteps. From wearing coats that blend in with Christmas decor to carrying handbags that seem way out of place for a public servant's wife, these are some of the first lady looks that gave worst-dressed a whole new meaning. 

Melania Trump has had her fair share of big fashion fails, but it seems like she was seriously in the spirit to celebrate Independence Day in 2018 when she sported a blue gingham gown-style dress from Ralph Lauren. While the dress itself was beautiful, the addition of the massive red bow as a cinched waist detail instantly made the ensemble look like a dressed picnic table. Honestly? She should've just worn the dress as-is with her hair up and completed the 'fit with red sandals for a festive and chic aesthetic. 

Michelle Obama might wear the pants in her relationship with Barack Obama, but the woman loves dresses. Colorful ones. And while some have been fabulous, her 2009 Inauguration Day outfit was perhaps too unharmonious. The head-to-toe green in all different hues might have been worn with good intentions to symbolize a fresh new start, but instead, the colors seriously clashed in every way possible and the outfit aged her quite a bit. From the matching lime coat and dress to the forest green shoes, it was just too much, it came together to create a chaotic palette that just didn't look right. 

Well-proportioned and tailored outerwear is crucial for public figures, and it seems Jill Biden and her styling team might have missed the memo for Christmas at the White House with the oversized red coat she wore. While the color was appropriate for Christmas, the shapeless and long coat overwhelmed her frame and created an unflattering silhouette. It's the kind of coat that would remind you of the giant red bows hung on front doors for the holidays. A fitted and structured red coat would have been much more appropriate and made a chic statement. 

Whether Hillary Clinton was first lady or a New York senator, she's had her fair share of outfits that left people confused. Clinton herself even poked fun at some of her cringe-worthy fashion moments in an interview with Us Weekly (via The New York Times). But perhaps one of our top contenders is the confusing outfit she wore to the 2004 Democracy for the Senate rally. The then-New York senator wore a sky blue knit top with a black power suit, then proceeded to top off the ensemble by tying a matching sky blue cardigan over her shoulders. Truly a Wall Street meets the Hamptons moment.

This Melania Trump outfit seriously takes 'worst dressed' to a whole new meaning, not because of the styling — she looks polished and chic as you can see — but because of her choice to carry an Hermés Birkin bag. The epitome of exclusivity and luxury, the gold 30 Birkin feels wildly out of place for a public servant's wife. It's a flashy statement piece that is totally appropriate as billionaire Donald Trump's wife, but definitely gives showy and tone-deaf vibes when you're the First Lady of the United States of America.

In 2015, Michelle Obama joined her husband on a brief trip to Saudi Arabia to give their condolences for the passing of King Abdullah. And while many criticized her for not wearing a headscarf (which may not be required but seen by many as a thoughtful gesture), our attention is completely elsewhere. We can't help but wonder why she chose to wear so much blue in a sea of black. While we understand the lady loves color, the vibrant hue made her stand out way too much, and it would've been better if she just wore a more subdued and neutral-toned outfit.

Hillary Clinton may have some stunning throwback pics, but we think she would agree that this isn't one of them. With such a petite figure, it's crucial for someone like Clinton to dress in flattering clothes, and this outfit she wore for a day out on the golf course missed the mark entirely. We're so torn on what distracts us more — the canotier hat with too thick of a rim or the khaki pants that look borrowed from her husband's closet. We will say the lime green knit-style top does complement her fair skin, so props to her for that. 

Alongside Jacqueline Kennedy Onassis, Nancy Reagan is often thought to be one of the most stylish first ladies, but not every day can be a fashion home run for even the best dressed. Style icons also have their off days, and for Reagan, this striped outfit just might be one of those moments that missed the mark. The striped two piece has just enough flare to flatter her figure, but the awkward white midsection creates a jarring contrast that disrupts the breezy flow of the outfit. On top of it all, the chunky gold necklace feels too oversized for the look. It's doing too much all at once. 

We're not sure if she knew it or not, but Hillary Clinton seems to have been way ahead in the trend game. Clinton wore the most unique Christmas-themed sweater to an event in 1998, and that was long before the ugly Christmas sweater craze took off and became a tradition in the states. And, she didn't stop there. She went all in with the accessories and wore a gold necklace with what looks like an angel or perhaps Virgin Mary pendant, paired with earrings inspired by Christmas ornaments. 

Jill Biden really had a message for everyone at a post-debate campaign rally in June 2024. The then-first lady wore a piece from Christian Siriano, a form-fitting black dress with "VOTE" written all over it. While we all understand the importance of her message, the bold lettering overwhelmed the outfit and felt more like a walking billboard rather than a fashion statement. It's important for there to be a balance when it comes to making a political point with your fashion choices, and this look just missed the mark on subtlety.