Kimberly Guilfoyle's Biggest Fashion Fails During The 2024 Campaign

Throwback photos of Kimberly Guilfoyle show that her outfits were awful long before she started dating Donald Trump Jr. You would think that a switch from Democratic beliefs to Conservative ones would mean longer hemlines, less cleavage, and generally more appropriate fashion choices. But you'd be wrong.

Since jumping on the Trump train, the former attorney has switched to revealing outfits, heavy makeup, and out-place accessories. This wouldn't be such a big deal if she had a talented stylist on her team to inform her choices, but judging by her appearances during the 2024 campaign, Kimberly Guilfoyle's stylist either secretly hates her or doesn't exist.

The talk show host's wardrobe typically features busy patterns, excessive jewelry, and cheap-looking fabric, often combined in the same outfit. When she isn't dealing with poor fashion choices, Kimberly Guilfoyle can be seen fixing wardrobe malfunctions that would probably have been easily avoided with the help of a style professional.

We're all for body positivity and wearing what makes us feel good, but there's no denying that certain occasions call for more appropriate attire — a memo Kimberly Guilfoyle repeatedly misses. At a Trump fundraiser at Mar-a-Lago in March 2024, the talk show host arrived in one of her most inappropriate outfits ever.

She wore a black dress with a plunging neckline dipping nearly to her belly button, leaving her breasts clearly visible under a see-through material. The dress also featured a thigh-high slit, barely covered by the same netting. It looked as if she had forgotten a scarf, cape, and jacket altogether.

Considering the event was meant to support a candidate who claims to have Christian values, Guilfoyle's outfit almost seemed like satire. One fan took to her Instagram comments to express their dismay: "Not campaign-appropriate. Perhaps late-night disco." Many more urged her to cover up and show more self-respect. Yikes.

Kimberly Guilfoyle's outfits aren't always short. In fact, during a visit to Utah with Don Trump Jr., she opted for a top and long pants, topped off with a cute but out-of-place pink jacket. The major problem? She paired the look with massive and glittery platform heels, even though they were visiting a barn. It almost seemed like the former attorney was intentionally leaning into the stereotype of ditzy women who wear glamorous accessories in situations that require practical outfits.

Guilfoyle definitely had other options, considering she claims to have around 500 pairs of shoes. Speaking to US Weekly, she shared, "One of the questions that I get asked all the time and I'm terrified to ... actually know the true answer. 'How many pairs of shoes do you have?' This is why it pays to be bad at math. The truth would frighten me. There have been estimates of about 500 pairs." 

The talk show host's visit to the Utah barn was to promote Donald Trump's agenda, but thanks to her fashion choices, she ended up sticking out like a sore thumb. Despite the "we love the working class" narrative she was peddling, it seems more likely that the concept of farmwork is foreign to her.

Kimberly Guilfoyle often struggles to strike a balance between short dresses that feel out of place and decent attire that doesn't look awful. At an America First event in July 2024, she wore a long-sleeve dress with a turtleneck. However, the issue wasn't the style; it was the bold, garish pattern, which appeared to be a poor attempt at mimicking Versace's signature intricate patterns. This loud, busy dress seemed even more out of place among the other attendees who wore simple, classy outfits. It's no wonder a fashion expert told The List that Guilfoyle is better off trading in-vogue trends for timeless style. Despite this advice, Guilfoyle obviously likes this particular dress, as she's been pictured wearing it on multiple occasions.

To make matters worse, the dress did little to flatter her figure. While it showcased her legs, the top created a square silhouette, making her upper half appear much heavier than her lower half. Fashion is certainly subjective, but there's no denying that this look did not complement her body's shape.

Trump's conservative fans seem to have accepted Kimberly Guilfoyle's complete style transformation, but even they cannot defend some of her choices. During a campaign event with Donald Trump on May 30, 2024, the former attorney's attire made her appear more like a waitress than an important member of the team. Dressed in a cleavage-baring dress adorned with flower petals for the lower half, Guilfoyle not only looked tacky but also inappropriate. She even completed the outfit with a flower choker around her neck, clearly leaning too heavily into the barmaid aesthetic.

Standing beside Donald Trump, who was fully dressed in a suit and tie, Guilfoyle seemed more like an entertainer, which is certainly a slap in the face of feminists who have fought for women to be taken seriously. One Instagram user was quick to voice their opinion in the comments: "Your attire in this picture is less than desirable. Choose classic over barmaid attire, really."

We're accustomed to Kimberly Guilfoyle leaving nothing to the imagination with her revealing dresses, but her appearance at a July 2024 fundraising event in Alabama raises the question: "How short is too short?" The former attorney arrived in a low-cut white dress that was so skimpy her inner thighs were clearly visible. Once again, she sharply contrasted with other guests who wore the same color but chose more appropriately modest outfits.

But beyond the too-short dress, another part of her appearance that stuck out was her heavy makeup. One commenter asked, "When is Kimberly going to start easing up on her eyeshadow? It's becoming way too dark and unbecoming."

There's no doubt that Kimberly Guilfoyle has the right to wear whatever she chooses, even if some consider it indecent, but it's interesting that she exercises her rights, while advocating for a candidate who helped overturn Roe v. Wade, disregarding the same autonomy for other women regarding their bodies.