Outdated Trends Kimberly Guilfoyle Can't Stay Away From

Kimberly Guilfoyle is an interesting one. Not only is she completely Guilfoyle completely unrecognizable in pictures before her Trump days, having 100% leaned into the Mar-A-Lago face trend, but she willingly dated Donald Trump, Jr. for six years before he left her for another women in 2024. Since then, many of Guilfoyle's outfits have screamed revenge as she's tried to publicly recover from her broken heart and move forward.

But trying to get Don Jr.'s attention with over-the-top, look-at-me ensembles is just the tip of the iceberg when it comes to Guilfoyle's tragic sense of style. The reality is that pretty much every day of her life Guilfoyle goes out into the world as if she's completely oblivious to what planet she's on, let alone what era she's living in. From a tacky outfit that we'll never forget to the cringy fashion and beauty trends she won't give up, Guilfoyle seems to never miss the opportunity to confuse the public with her choices.

While Guilfoyle has worn the occasional surprising outfit that proves she must be taking the internet's advice, for the most part, she wears whatever she wants. Although that could be admirable, but considering how so many of those things are epically outdated — and not in a good way — it makes any admiration moot. Like Pam Bondi's outfit that was ripped from the '70s, Guilfoyle, too, struggles to say relevant and in style with the majority of her looks.

As of fall 2023, cutouts dresses are totally outdated. However, Kimberly Guilfoyle doesn't seem to care — or maybe she doesn't know. Although the caption for this 2024 post calls this picture a throwback, based on the look of Guilfoyle's makeup, the photo isn't old enough to make the dress 'vintage.' It's also worth noting that this white cutout number is just one of a whole boatload of outdated cutout dresses that Guilfoyle has worn.

In June 2025, Kimberly Guilfoyle attended the Monaco Grand Prix and appears to have brought with her not one, but two feather jackets — one in baby pink and one in black. There are only two occasions that would call for such a piece in 2025: Halloween or as a nod to old Hollywood glamour while on the red carpet. As we can see, neither is the case for Guilfoyle. While feather jackets and stoles were big in the 1920s and had a resurgence in glitzy disco days of the 1970s, today they're simply passé for everyday wear.

The 1990s and early aughts were all about chokers, so much so that brands even started making them part of tops and dresses. While a choker is a fun jewelry trend to channel sleek '90s redux, the shirt version is so archaic that it fails to channel even low-key cool vintage. But despite this, Kimberly Guilfoyle has a lot of tops with this style neckline, proving that she's still stuck in the past.

If you're familiar with Kimberly Guilfoyle's summer style book, then you've probably noticed she just loves white open-toe platform sandals. While there are plenty of options for staying chic in your 60s and beyond, Guilfoyle's idea of staying fashionably hip seems to be wearing this outdated shoe trend. If this were the early 2000s, then these sandals would make sense, but it's 2025. The world has moved on to more practical sandals.

Although we're glad that Karoline Leavitt ditched this outdated 2000s hair trend, Kimberly Guilfoyle is still embracing the Bumpit look. The look was everywhere in the early 2010s, with everyone from the "Jersey Shore" cast to your neighbor going for the high-volume look. Of course, that highly stylized era would fade away around 2020, with more people turning to natural styles. However, it appears as of 2024, Guilfoyle still hasn't let it go.
Hopefully, she'll soon follow Leavitt's lead.

Before his death in 1997, Gianni Versace was one of the most important designers of the 1990s. One of the things he was known for was big bold patterns on skin-tight, mini dresses with high necks that were reminiscent of his autumn/winter 1992/1993 bondage collection. Because of how iconic Versace was, a lot of knockoffs came into fruition during that decade, many of which looked like this black and white get-up Kimberly Guilfoyle is trying to make work. If you're of a certain age, you know this dress reeks of the 1990s, but not in a good way.

If there ever were a place to embrace the full revival of Y2K fashion trends, Kimberly Guilfoyle's closet is it. Further proof of this is in her affinity for peplum dresses, of which she seems to have a ton of and in every color. Peplum dresses and tops were one of the big business casual looks that dominated the mid aughts and early 2010s. While designers would later deliver their own haute couture take on the trend, as Alexander McQueen did in their spring 2012 ready-to-wear collection, it never really had staying power.. By the time 2020 came around, most had declared the style finished. However, Guilfoyle clearly feels otherwise, as evidenced by this 2022 photo.

One could argue that blazers are a piece that never goes out of style. However, over the years, the specific fit and cut has changed with the times. Though there was a time figure-hugging styles were en vogue, by the time the late 2010s came around, oversized styles had become the norm. As such, Kimberly Guilfoyle wearing a fitted pastel blazer in 2020 couldn't be more out of touch with the times. The only thing that would make this look more outdated is if it were paired with skinny jeans.

When it comes to the skinny jeans debate, there are people on both sides. For example, you can style your skinny jeans so you don't look outdated or you can pull a Lauren Boebert, refusing to give up the outdated denim trend, and make zero attempts to elevate the look. Kimberly Guilfoyle opts for the latter of these choices. Despite the skin-tight denim being ostensibly out of style since the late 2010s, the conservative news personality wore them proudly in 2020 to a football game — complete with a chunky belt and all. 

Throughout the 1980s and 1990s, logo-mania was everywhere. The look wasn't just the nouveau riche crowd, as the middle-class were indulging in the trend by buying knockoff designer items with similar insignia. Then around 2010, going logo-free became the true statement of sophistication and luxury. As stealth wealth moved in, it eschewed those who had the audacity to flaunt logos in a tacky and outdated way. However, that memo seemed to miss Kimberly Guilfoyle. In March 2023, she posted a photo of herself and Lara Trump that showed her wearing a Chanel ensemble with a big double C brooch on the lapel. In other words, Guilfoyle proved again she's a sucker for an outdated trend, but never ironically so.