The Most Inappropriate Outfits At Political Events That Left Us Stunned

Over time, fashion standards have become far less strict in the American political arena — long gone are the days of Jackie Kennedy's tailored sophistication and Nancy Reagan's designer elegance. As the rules of etiquette have become more relaxed and the definition of "formalwear" more open to interpretation, it's no surprise that some tasteless and tacky looks have slipped through the cracks in Washington, D.C. It seems that no matter the political event, there's at least one prominent figure wearing an eyebrow-raising look, whether it be a far-too-revealing dress, a tone-deaf fashion statement, or something just plain ugly.

It's one thing to be Ivanka Trump in her slew of outdated trends or White House Press Secretary Karoline Leavitt in her frumpiest work outfits, but when you show up to a political event dressed like it's buy-one-get-two Friday at the club, then it's safe to say you've lost the plot. If you've ever wanted to know how not to dress for a political event, then look no further than these outfits — and make sure to do the exact opposite.

Kimberly Guilfoyle has made it abundantly clear that she doesn't know how to dress herself. From the tacky outfit that we'll never forget to the gaudy dress style she can't seem to give up, Guilfoyle clearly doesn't own a mirror. Or she does, but it hasn't been properly cleaned in quite a few years. To prove this mirror theory, in March 2024, Guilfoyle wore this shockingly low-cut dress, with a hip-high slit to boot, while campaigning for Arizona congressional hopeful Abe Hamadeh. While there's nothing wrong with a little cleavage (or even a lot), this certainly wasn't the place for it.

If anyone can pull off the topless blazer look, then they should definitely be applauded for being so fierce. However, there's a difference between that and wearing a blazer that specifically showcases your bra at a major political event — because it's not the same look at all. But someone didn't tell that to Jeff Bezos' fiancee, Lauren Sanchez.

So, on January 20, 2025, for Trump's inauguration, Sanchez, who apparently thinks she's Carrie Bradshaw with the way she had her lace bra fully on display, stunned viewers with her outfit choice. If that weren't enough, the New York Post published a handful of screengrabs of Mark Zuckerberg and others enjoying the view.

From her affinity for outdated accessories to all her outfits that have missed the mark, it goes without saying that Karoline Leavitt is a fashion lost cause. So, when Leavitt attended the Conservative Political Action Conference (CPAC) on February 21, 2025, embracing the mob wife aesthetic of 2024 by wearing a leopard dress and knee-high black boots, no one should have been surprised. During the event, Leavitt was interviewed by former White House Director of Strategic Communications Mercedes Schlapp, who at least made an attempt to look professional.

Eric Trump's wife, Lara Trump, has a hard time reading the room when it comes to dressing appropriately. Take a look at this skin-tight cut-out dress she wore to the Curetivity Charlotte Golf Invitational to support St. Jude Children's Research Hospital. There's nothing bad about the dress, per se, other than it's ugly, and the cut-out portion on Lara's midriff is awkwardly placed and totally unnecessary. A charity event seems like an inappropriate venue for Lara to bare some skin, and the look was nothing if not distracting.

Is it even a list of inappropriate outfits at political events if Lauren Boebert isn't included? No way. Boebert loves to wear outfits that are complete misses, refuses to ditch unflattering hairstyles, and if you need a lesson in beauty mistakes, you can count on Boebert for that, too. That being said, it should come as no surprise that Boebert would attend CPAC and talk to the United States Permanent Representative to NATO, Matt Whitaker, while wearing a bright pink mini dress. And, in true Boebert style, she paired the dress with her go-to ill-fitting blazer because, as they say, a tiger can't change its stripes.

In February 2017, Donald Trump made his first congressional address. His speech centered around the slogan "buy American, hire American," which many found hypocritical considering Ivanka Trump's attire. The First Daughter donned a pink gown from French designer Roland Mouret, which was made in the UK. Though the $3,000 price tag is far less than most of her other outfits, Ivanka clearly missed the memo about the evening's topic, or she would've worn a dress designed and made in the U.S. She sparked even more criticism when members of the public pointed out that much of her own clothing line is made overseas in China, Indonesia, and Vietnam.

Arkansas Governor and former White House Press Secretary Sarah Huckabee Sanders made a huge fashion faux pas in December 2022 when she re-wore an outfit that had already earned her plenty of criticism. The loosely ruffled dress was deemed far too casual for a campaign event, but the look appeared just as out of place next to the Arkansas state police a few months later — especially with the knee-high boots. We likely won't see her grabbing this piece out of the closet again if she listens to the horde of critics in her comment section. However, Huckabee Sanders made the same mistake in 2025 by re-wearing another outdated trend, so who knows?