Kimberly Guilfoyle Outfits That Were Beyond Tacky

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If there's one thing many can agree on, it's that Kimberly Guilfoyle has eclectic taste. From outdated trends she can't stay away from to the times her outfits screamed revenge after she and Don Jr. split, Guilfoyle continues to evoke side-eyes with her fashion choices. In fact, it's Guilfoyle's unique sense of style that may have played a role in her being dumped by Don Jr. in 2024.

According to People, an anonymous source told the magazine that Don Jr. sees his new partner, socialite Bettina Anderson, as someone who will fit in better with his family; a step up from Guilfoyle, so to speak, and more in line with Melania Trump. Even before it was made public that Guilfoyle and Don Jr. were no longer together, the latter had been complaining about his partner's looks being too uptight and never casual enough. While uptight is definitely a choice word when describing what Guilfoyle wears, the source added, "The tight dresses need to go, and she has been told that."

While Guilfoyle may have been told what she shouldn't be wearing, it doesn't seem like she'll listen. After all, this is a woman who almost appears to pride herself on not giving up certain cringey fashion and beauty trends, no matter how tacky. And you know what? Good for her. Don't let them break your tacky spirit, Kim!

In May 2025, Kimberly Guilfoyle attended the 31st amfAR Gala in Cannes in a look that channeled the dancing lady emoji. Considering amfAR is the foundation for AIDS Research, one would think Guilfoyle might have been more mindful of her attire, but that didn't happen. Instead, Guilfoyle decided to make the night all about her and her distractingly busy red dress. It looks like whoever designed it changed their mind halfway through, taking it in multiple strange directions with sheer mesh panels, beading, puff sleeves, and a large slit. As if the dress wasn't bad enough, Guilfoyle accessorized with a silver clutch and silver platform sandals, which brought more eye-catching attention to an outfit that already had plenty.

As much as we should all be freeing ourselves (and our breasts) with the benefits of going braless, unfortunately, there's a time and a place. This is especially the case when you have large breasts like Kimberly Guilfoyle. While no stranger to skipping bras — an admirable quality in anyone in a culture that wants things strapped down and managed — both the fabric and cut of Guilfoyle's dress failed her. The added lighting highlighted how uncomfortable she looked, delivering another tacky moment that Guilfoyle could have avoided if she'd chosen a different design, a better fit, and avoided that light.

For the August 2018 premiere of "Death of Nation" in Washington, D.C., a not-quite-Mar-A-Lago-face Kimberly Guilfoyle wore a skin-tight white dress with one of her favorite details: a plunging neckline. But in reality, it's not about the neckline; it's about the sheer, bedazzled overlay that added another complicated element to an already-detailed look. It also looked like she was trying to minimize the appearance of the plunge, which was the focal point of the dress itself. If you're going to wear a dress like this, embrace what you're showcasing.

Similar to Kristi Noem, Kimberly Guilfoyle is guilty of making herself look older by dressing like a teenager. When Guilfoyle attended an event for the Memorial Day Issue of Social Life Magazine, she showed up in a belly-button-revealing crop top and bright red cropped trousers. While we can see the patriotic color story she's trying to tell, it's the wrong outfit for the event. While crop tops have no age limit or body shape requirements, they can still come off as tacky, especially at photo-ops. You simply don't attend an event in the Hamptons dressed like you're 17 years old and heading to a Memorial Day BBQ.

As we saw in January 2025, Kimberly Guilfoyle's inauguration looks are some of her most questionable, and her choice to wear a floor-length flapper dress to a formal event ranked high on the tackiness scale. Granted, Trump's inauguration was a sea of stars and politicians whose outfits totally missed the mark, but her overly embellished, multi-tiered look left us scratching our heads. What made things worse was how she accessorized it with a large rhinestone cross necklace, which even the most pious might agree is too much. Surprisingly, Guilfoyle kept her hairstyle low-key, ditching the outdated 2000s hair trend Karoline Leavitt loves: the Bump It.

Although one can suggest that Kimberly Guilfoyle needs a stylist, the one place where she truly excels is in her love for animals. In 2024, Guilfoyle partnered with Brave Books and published her first children's book, "The Princess & Her Pup." For the launch, Guilfoyle wore a white sequin A-line dress with a feather hem and bodice on top. It was an odd choice for an adult, especially for such an occasion. While people should dress however they want on their book launch day — it's a huge day, after all — her look screamed 'matrimony' instead of 'published author.'

On September 18, 2025, Kimberly Guilfoyle was officially confirmed as the next U.S. Ambassador to Greece. With the announcement came well-wishes from colleagues and fans alike, and Guilfoyle was tagged in photos across Instagram. In one of those photos, Guilfoyle is pictured at an event wearing a strapless black dress with several cutouts. Although cutout dresses were totally outdated for fall 2023, the real crime isn't just the cutouts, but also the dropped-waist adorned with ruffled layers, which made for yet another confusing outfit that looked more suited to a nightclub. We may not know the exact reason for this event, but we know tacky when we see it.

Does Kimberly Guilfoyle love a sparkle or two? You better believe it. For Mother's Day 2025, Guilfoyle posted a carousel of photos of her and her son, and each look was tackier than the next. But one outfit stole the show: a periwinkle dress with large puffy sleeves, cutouts, and sparkling silver bows across the bust. Paired with equally glitzy hoop earrings, this outfit was next level in all things gaudy. We may not be able to expect Guilfoyle to give up the cutout dresses, but the attempt at pulling off the now-outdated coquette beauty trend reads as both frumpy and juvenile.

If you ever wondered what Kimberly Guilfoyle would wear to an event for a nonprofit animal rights organization, you might be surprised by her sartorial instincts. While at first, Guilfoyle looked like she might be cosplaying as famed antagonist Cruella de Vil, the reality is that she thought a black full-length gown with a belted dropped waist, feathered skirt, and plunging lace bodice was the best look for the event. And because the dress isn't busy enough, Guilfoyle completed the look with big earrings and a long, chunky necklace ending at her cleavage. Considering she dressed like a villain to support a no-kill shelter, this may be her tackiest look yet.