Outrageous Outfits at Political Events That Left Us Speechless

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 — or even a lot of cleavage — this isn’t the place for it. However, Hamadeh won and is now a U.S. representative for Arizona’s 8th congressional district, so maybe the cleavage was the key ingredient to his success.

While Ivanka Trump likes to pretend she’s empathetic, even posting her support for the LGBTQ+ community on X, formerly Twitter, in 2017, the apple actually doesn’t fall too far from the tree in her family. In January 2017, Trump posted a photo of herself and husband, Jared Kushner, in which she wore a $5000 silver Carolina Herrera gown. Trump wore the dress to the annual Alfalfa Dinner at the Capital Hilton, a political event that included music by the U.S. Marine Band.

What made Trump’s outfit so inappropriate was that her dad had just banned Syrian refugees and Muslim immigrants from coming into the U.S., and here was Trump showing off her lavish lifestyle while human rights were being taken away. The dress would come under fire again when people noticed how much it looked like the thermal blankets that the immigrant children — many of whom had been taken from their parents — were using in the Department of Homeland Security’s detention center.

According to the World Health Organization, by the time the week of December 29, 2020, rolled around, 79 million cases of COVID had been reported, and 1.7 million deaths had occurred globally. Despite that, Karolina Leavitt — like the rest of the MAGA inner circle — attended the White House Christmas Party that year wearing a skin-tight, glittery dress and, of course, no mask. Although this dress is one of her spiciest outfits that clash with her press secretary persona, what makes it inappropriate is, for starters, this isn’t exactly something to wear to a work holiday event, and, secondly, people are dying, Karoline.

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 — 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 — at least according to MAGA standards.

Eric Trump’s wife, Lara Trump, has a hard time reading the room when it comes to dressing appropriately. However, because a lot of those times weren’t exactly political events, like this getup she wore to a New Year’s Eve party at Mar-A-Lago in 2024 and posted on Instagram, it hurt a bit to have to exclude so many of her jaw-dropping looks. Luckily, we have this skin-tight cut-out dress that 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. St. Jude exists to find treatment for sick children, especially those with life-threatening diseases like cancer, so it seems like a strange outfit for Lara to wear while representing the Trump family in support of such an important cause — not to mention 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.

Not long after Donald Trump’s second presidential win, his daughter Tiffany Trump posted a photo of the whole family on her X account. Well, it was the whole family minus First Lady Melania Trump and plus Elon Musk. While none of the people in the photo will ever be remembered for their fashion — or much of anything positive and kind, for that matter — there are two standout looks. For reasons humanity may never know, Ivanka is wearing a blue monochromatic velvet suit, and it’s simply awful. Also, there’s Lara Trump in a mesh top that’s far too sheer for the event. Again, why this was chosen may remain a secret forever, and that’s honestly A-okay — but it still doesn’t make it appropriate.