Kimberly Guilfoyle's Worst-Dressed Moments During Trump's First Term

Kimberly Guilfoyle is known for her polarizing fashion choices. Now that she's serving as U.S. Ambassador to Greece, Guilfoyle has switched up her wardrobe a bit and added a succession of Kamala Harris-esque pantsuits. However, Guilfoyle's also stayed true to her old ways and showcased some skin-tight outfits in Greece. "Ambassador of bad taste," joked one Instagram user, alongside a video clip of Guilfoyle posing in a bedazzled minidress.

While it may seem like Guilfoyle's fashion has always followed this tacky template, she's gone through a lot of changes in the decades she's been in the public eye. For instance, when Guilfoyle and Gavin Newsom were married in the early 2000s, her style was often understated (although she did display some modest glam in a September 2004 Harper's Bazaar photo spread). After she left her legal career and joined the team at Fox News, Guilfoyle's fashion preferences shifted more dramatically. Both in and out of the studio, Guilfoyle appeared in more form-fitting dresses, some with shorter hems and lower necklines.

Although her style has steadily evolved, some of Guilfoyle's fashion missteps have long roots. While her allegiance to skin-baring, revealing 'fits reportedly proved to be a thorn in Donald Trump Jr.'s side (per People), even in her pre-Trump era, Guilfoyle stepped out in a selection of bad outfits. Some of those past mistakes included issues with animal prints and transparency. Fast forward to 2017, when Donald Trump entered his first presidential term, and similar mistakes were still evident in Guilfoyle's attire.

Even though Kimberly Guilfoyle and Donald Trump Jr. weren't dating yet, Guilfoyle's connection with the family was strong enough to score an invite to one of their 2017 inauguration celebrations. The then-Fox News host pulled this confounding dress out of her closet for the occasion. The neckline's embellishments look like an odd, oversized statement necklace. Even with the knee-high slit, the gown's mermaid skirt looks like it would have been problematic on the dance floor. However, the dress was clearly a favorite of Guilfoyle's that year, since she wore it a few months later to a country club gala. 

In May 2020, Kimberly Guilfoyle gave fans a glimpse inside her kitchen as she cooked up a special Cinco de Mayo meal. While her Mexican lasagna looked delicious, her top was a fashion disaster. The yellow and purple print looked like animal print and had some followers thinking it was subtle fan gear for the Louisiana State University tigers sports teams. Colored prints can be hard to pull off, and the unflattering cut of the shirt made things worse. The long length obscures Guilfoyle's waist, and the super-puffed sleeves distort her silhouette further.

In April 2019, Kimberly Guilfoyle attended a New York Fashion Week event in this color-blocked ensemble. Taken separately, these two pieces are fine. Unfortunately, when they're together, it looks like she closed her eyes and picked them at random. The skirt's sharp asymmetrical hem clashes with the softer line of her ruffled top. Instead, Guilfoyle might have chosen a brighter orange skirt with a similarly ruffled hem to wear with the shirt. Or, she could have ditched the top and paired this skirt with a tailored button-down in navy or teal.   

Kimberly Guilfoyle tried too hard to mix and match her wardrobe the year prior as well. At a May 2018 event for Social Life Magazine, Guilfoyle ended up with a confusing 'fit that revealed her toned abs. While the top skews formal, its shorter hem doesn't work with lower-rise pants. Guilfoyle's necklace also adds to the disorienting look, since the super-long chain and pointy pendant acts like an arrow that draws even more attention to her exposed belly button. Separate, these pieces are fine. They just don't work together.

With one strategic alteration, Kimberly Guilfoyle's Christmas 2020 dress could have been a fashion win. The black gown hugs her curves and has a plunging V-neckline that stops before it goes too far. Unfortunately, the bottom trim takes the dress into tacky territory. A bit of fringe might have been fine on its own, but the addition of sparkly sequins goes overboard. 

Things weren't better earlier in the month when Guilfoyle went for a pantsuit for another holiday celebration. The jacket clearly needed a shell top underneath. The low neckline had Guilfoyle on the brink of a serious wardrobe malfunction.

Kimberly Guilfoyle's leather dress seemed like it was made for the club, rather than a January 2017 youth charity event. Maybe Guilfoyle had plans after? If so, she'd have been better off changing. The non-stretchy material looks difficult to walk in, especially since this dress has a bodycon silhouette. However, Guilfoyle doesn't seem to be daunted by uncomfortable fashion. Years later, she celebrated Christmas 2023 with a similarly constrictive dress, proving that both she and Sarah Huckabee Sanders have a fandom for leather 'fits.         

Kimberly Guilfoyle has a longstanding relationship with the designer Zang Toi. In 2019, she supported Toi by attending his show at New York Fashion Week. Unfortunately, the butterflies on her shoulder weren't able to distract from the dress's unintentionally revealing fabric. At some angles, the knit looks like it provides adequate coverage.  Head on, it's a very different story, and the bright lights accidentally put Guilfoyle's bust in the spotlight. While this might be Guilfoyle's most infamous see-through dress, she also wore a similarly sheer gown to one of Donald Trump's cabinet dinners in January 2017.