5 Outdated Outfits Kimberly Guilfoyle Was Caught Wearing

Kimberly Guilfoyle, former Fox News host and fiancée of Donald Trump Jr., has become known for her less-than-stellar fashion sense. That's because there are a lot of mistakes Guilfoyle makes with her style and a lot of reasons why her choices are often flops. One of the biggest problems is her love of trends and apparent disregard for whether said trends are actually current. While Guilfoyle has had a style transformation over the years, that doesn't mean she's keeping up with the times, and this is one of the biggest reasons why she needs a fashion makeover. 

While her wardrobe may be totally stuck in the past, Guilfoyle's life is moving forward. It seems that she may be heading into 2025 single, as Don Jr. reportedly ditched her for his alleged mistress. Donald Trump has also nominated her as the new U.S. ambassador to Greece. As she moves into what is likely to be a transformative new year, there are plenty of fashion and makeup mistakes we're begging Guilfoyle to ditch in 2025. 

First on the docket? That would be her penchant for wearing out-of-date looks. So, we've gathered some of the most outdated ensembles she's worn over the years — and let's just say, it's some damming evidence that she's ready for a wardrobe overhaul.

Not only is a blazer and jeans a classic outfit combo, but it's a great choice for a football game. Since Kimberly Guilfoyle seldom seems to choose an outfit that's appropriate for the occasion where she's wearing it, it's only fair that we give credit where credit is due. Still, Guilfoyle somehow managed to sport this classic outfit in a way that was majorly out-of-style. Guilfoyle wore a white blazer with dark jeans to the Super Bowl in 2020. At this time, skinny jeans were already on their way out. Tucking them into boots exacerbates their skinny cut, and therefore, it feels even more outdated than untucked skinny jeans. 

The jeans of choice, on their own, felt like an outdated pick, but she took it a step further by pairing them with a long top and a chunky belt layered on top. This was a trend around 2007 and 2008, and just seeing it totally takes us back to that time. Ditching the belt and tucking the top into some high-rise, baggier-fit jeans would have totally updated the look and made it feel fresh.

Kimberly Guilfoyle loves a skin-tight mini-dress. While most of us consider this to be a look that's exclusively appropriate for a night out, Guilfoyle seems to think of it as the perfect go-to outfit for every day. This outfit Guilfoyle posed in for an Instagram pic certainly doesn't look fresh or stylish, but there was a time when it would have looked on-trend. This look is so Kim Kardashian in 2010. Unfortunately, Guilfoyle did not wear this dress in or around 2010. She actually wore this to wish her Instagram followers a "Happy New Year" in 2024. 

Nothing about this look is really working. The color washes her out and feels off-trend. The bedazzled pattern looks tacky, and the over-the-knee boots just don't work with the rest of the look. Ditching the rhinestones and swapping the beige hue for a bold jewel tone would have improved the dress and accessorizing it with some sheer black tights and knee-high black boots, and a high ponytail would have preserved the vibe she was going for while giving it a much more up-to-date feel. Instead, she started the year off on the wrong foot, having already sported one of her worst looks of 2024 on day one. 

Anyone who knows Kimberly Guilfoyle knows that her New Year's 2024 bedazzled mini-dress was far from an isolated incident. A year prior, in January 2023, she went for a similar, equally outdated look. She sported another long-sleeve minidress — this time with even more garish bedazzling. The busy pattern was comprised of glitzy martini glasses: a print she didn't just wear once but also wore in a lighter shade of pink for Valentine's Day the following month. 

This dress' hue, fit, and copious rhinestones can't help but remind us of something Paris Hilton may have sported back in 2004. Once again, this look wasn't at all modern enough for when she chose to wear it. As she is wont to do, she also managed to make it even worse with her styling. The matchy-matchy clutch bag, the big dangly silver earrings, and the extra-long hair extensions all made her look stuck in the past.

Peplum is a style that's gone in and out of trend for decades. While the distinct ruffle around the waist has been around for as long as we can remember, it's divisive, and at any given time, it's either very in or very out. The style was one of the biggest trends around 2010, but it seemed to go away just about as quickly as it arrived. Leave it to Kimberly Guilfoyle to sport it a decade later.

In 2020, Guilfoyle wore exactly the kind of tight peplum dress you might have seen on a Forever 21 mannequin back in 2010. She sported the silhouette in a bold seafoam green while speaking at a campaign event for Donald Trump, and it wouldn't take someone who knows a lot about trend cycles to know that this stuck out like a sore thumb. Like many of Guilfoyle's looks over the years, her choice to rock this particularly trendy style so long after it was no longer a trend just proves that she'd look so much better if she opted for classic silhouettes.

We all know by now that low-rise pants have made a comeback, whether folks like them or not. In 2018, though, low-rise was firmly out, and high-waisted garments were in. However, this was the year when Guilfoyle attended a Social Life Magazine event with her belly button fully exposed in a truly statement-making look. Even now that low-rise pants have come back in fashion, this outfit would still strike most people as bizarre. It's both business casual and strangely revealing. If the top was slightly longer, this would have worked for a day at the office. As it is, though, this outfit basically doesn't work for any occasion we can think of. 

The silhouette of the pants and the extra-long statement necklace also helped to make this look feel like the ghost of trends past. Swapping the pants out for a wide-leg, high-waisted navy option and ditching the necklace would have actually turned this ensemble from outdated to chic and made her look fashion-forward.