She may not be a household name like Donald Trump, but Kimberly Guilfoyle has become one of the most prominent voices in conservative circles. That’s partially because she was once fiancee to Donald Trump, Jr., and she got to know this prominent family very well. And it’s partially because she parlayed those connections to land one of the world’s coolest jobs as America’s Ambassador to Greece.
Her quasi-celebrity status and big-time government position mean that Guilfoyle must constantly be in front of the cameras. Fortunately, she usually has a solid fashion sense and rocks the kinds of fearless fits that women everywhere would kill to pull off. However, when Guilfoyle has a fashion fail, it’s so bad that we start to wonder whether she even knows her way around her own closet.
What kind of fails are we talking about, and just how badly did this conservative queen embarrass herself in front of her biggest fans? Keep reading to discover Kimberly Guilfoyle’s weirdest fashion fails of 2025!
Bows with blouses? Girl, please!
Sometimes, it can be hard to spot a real fashion faux pas. If you don’t know the intricate rules of fashion, for example, you might not realize when someone has made a small mistake. Other times, though, someone screws up in a way so obvious that pretty much everyone can recognize it. And that’s what happened when Kimberly Guilfoyle met Secretary of War Pete Hegseth while wearing a blouse covered with bows.
For women, this is the fashion equivalent of a guy wearing both a striped tie and a striped shirt. Her whole fit looked impossibly cluttered, and Guilfoyle herself looked like something between a gift-wrapped present and a waitress at a pirate-themed restaurant. It doesn’t help that she has a pinched look on her face, as if even she’s not sure why she wore such a weird outfit.
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Dressing like a teenager
With most fashion fails, we can usually get an idea of what someone was going for. Like, they may fall short of the mark, but we can visualize what they thought an outfit was going to look like. There are some exceptions, though, including the time that Kimberly Guilfoyle posed with her son on Mother’s Day, 2025, prompting us to wonder whether she wanted to dress more like the boy’s mother or his sibling.
You see, Guilfoyle skipped some of the more sensible options like a professional dress or a pantsuit in favor of wearing a short, pink minidress, complete with a white Peter Pan collar. The whole visual effect is that of a coquettish schoolgirl, an aesthetic that seems completely at odds with her position as one of the most influential government employees in the world. And considering that her outfit may very well violate rules about dress length at her son’s school, we are still flabbergasted that she chose to look like this for a sweet Mother’s Day photo!
Looking silly in sequins
You want to know what’s even weirder than wearing bows with blouses? Simple: wearing too many sequins as part of your outfit! Unfortunately, this is another fashion faux pas that Kimberly Guilfoyle walked into, this time while attending her own party. You see, she was getting ready to move out of America altogether and live in Athens as part of her new job as Ambassador to Greece. In getting ready for her own going-away party, Guilfoyle decided to wear something truly memorable.
Unfortunately, it was memorable in all the wrong ways. That’s because Guilfoyle wore a black dress that would have been cute enough on its own, but she paired it with a huge chain with equally oversized sequins on it. It’s a wild look…like, she genuinely seems more like someone cosplaying than a conservative celeb attending her own party. Everyone’s eyes were on her the entire evening, and that may very well have been what she was going for. But we can’t help but wonder, isn’t it better to wear a forgettable outfit than one everyone remembers for being so garishly over-the-top?
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From tiers to tears
When it comes to Kimberly Guilfoyle’s most recent fashion fails, it’s fair to say that we saved the weirdest for last! This past November, she posted a photo of herself to Instagram in which she was wearing a truly crazy outfit. Specifically, she rocked a sparkly, cream-colored gown that was absolutely covered with a wacky combination of ruffles and sequins.
On top of this, she wore a cross so big that we were half-expecting her to crucify herself. Of course, she did get crucified on social media, where haters derided her for looking like a child dressing herself for the very first time. Others dragged her for failing Fashion 101 and wearing a tiered dress that seemed like a cross between a princess and a pastry. Once again, this was a memorable outfit in all the worst ways, prompting even Kimberly Guilfoyle’s biggest fans to wonder what the heck she was thinking.