Kimberly Guilfoyle Needs To Give Up On These Cringey Fashion & Beauty Trends

Despite being briefly married to democrat Gavin Newsom from 2001 to 2006, Kimberly Guilfoyle is now very much a part of the MAGA movement. From 2018 to 2024, Guilfoyle was in a relationship with Donald Trump, Jr. and most recently was nominated by Jr.'s dad to be the US ambassador to Greece. In other words, Guilfoyle is in deep with that crew and has the ever-popular Mar-A-Largo face to prove it.

In addition to her plastic-surgery-gone-wrong look, Guilfoyle has exhibited traits that are consistent among the women who are either in the Trump administration or have close ties to it: cringey fashion and beauty trends. There's Pam Bondi's undeniable passion for unflattering pantsuits, Karoline Leavitt's penchant for frumpy work outfits, and, of course, Lauren Boebert and the beauty mistake she won't stop making: cakey foundation. For reasons that science has yet to study, it seems that anyone who works closely with Trump struggles to do political fashion in a way that keeps up with the times. Guilfoyle is in that group. From hair extensions that need to be surrendered to her love affair with 2000s style logomania, Guilfoyle is a walking in lesson in how not to dress if you want to be taken seriously.

As much as hair extensions are a fantastic way to make hair look fuller and longer, they can sometimes be too much. When that happens, you not only end up with a head of hair that's obviously not yours, but you bypass the whole point: hair extensions are supposed to look 100% natural. However, Kimberly Guilfoyle seems to have not received that memo because her extensions go on and on for days, putting her in the celeb hair extensions that make us cringe club. There's no shame in wearing hair extensions, but when they start looking ratty and no longer blend in with your real locks, it's time to ditch them.

Don't get us wrong: this tacky dress is absolutely fun in all the best ways. With its super-plunge neckline and hip-high slit, both of which are covered in a netting type of material, it's exactly what you'd wear to the club when the theme is "Jersey Shore" night. But in March 2024 when Kimberly Guilfoyle chose to wear this very 2010s getup, not only was it not "Jersey Shore" night, but she wasn't even at the club. Instead, she was campaigning for Arizona Congressman Abraham Hamadeh. Guilfoyle actually pulls out the club wear for a lot of political-related events and it needs to stop. Save it for da clerb where we all fam, Kim.

Although the whole mantra of dressing your age is dead — thankfully! — there are ways to stay chic in your 60s and beyond that are worth noting. The first step toward doing that is admitting you're no longer 21, something that Kimberly Guilfoyle struggles with a lot. While Guilfoyle may not be 60 just yet, with this floral bandeau top, snug skirt, and sky-high platform sandals, she looks like she's going to brunch with her college-age girlfriends back in 2010. If Guilfoyle could embrace her reality for a hot minute and stop clinging to the past, it would serve her well, fashionably speaking.

Remember the mob wife aesthetic of 2024? Of course you do because it was a lot of fun and who doesn't love dressing like Adriana La Cerva from the "Sopranos" from time to time? Well, Kimberly Guilfoyle lives for the mob wife aesthetic so much so that skin-tight, mini dresses like this one appear to be a staple in her wardrobe. She also leans into heavy makeup no matter the time of day or season. It's time that Guilfoyle let this whole trend go and, as Tony Soprano himself would say, fuhgeddaboudit.

If you haven't seen Kimberly Guilfoyle before her Trump days, you'll be in for a shock because she looked wildly different. But like a lot of people, she drastically altered her appearance once she got a taste of the spotlight. Many have speculated that she received plastic surgery.

Although the congresswoman has never confirmed this, what is evident is that she remains heavy-handed with her makeup. In this photo, she's wearing thick dark eyeliner, fully filled eyebrows, over-lined lips, and heavy contour in broad daylight. The intense look harkens back to the mid 2010s, when beauty influencers were posting tutorials galore on how to achieve Instagram face. But given how makeup trends have changed drastically since 2015 — with many opting for a more natural look — this aesthetic is wildly out of place in 2025.

During the late aughts when Y2K fashion trends were all the rage, there was a plastic hair accessory called the Bump-It that was designed to add more thickness and volume to the crown of the wearer's head. At the time, when pulled back bangs were in style, this made sense. But as hair trends evolved, forced volume faded out in favor of more natural waves. However, it seems Kimberly Guilfoyle didn't get the memo, as evidenced by a 2024 photo of her with a noticeable lift on the back of her crown. 

When it comes to the outdated denim trend that MAGA women won't give up, you don't have to look further than skinny jeans. Like Lauren Boebert, Kimberly Guilfoyle continues to wear this form-fitting style like it's still 2009. Why these two can't let these particular dead-in-the-water trends go is something we may never get to the bottom of, but at least we can learn a lesson from them.

One of the most important things to come out of "Succession," other than how to diabolically insult your immediate family members, was how to live and breathe quiet luxury and old money aesthetics. The mindset behind this is just because you have money, you don't advertise it with logos and obvious branding, instead choosing classic, low-key designer pieces that will stand the test of time. It's a direct opposite to the early aughts, which was all about logo mania and flaunting your wealth with designer labels. Kimberly Guilfoyle, however, still loves a flashy insignia, as evidenced in the above photo from 2023. She has shown that she has zero qualms with advertising the designer behind her clothes and handbags. Shiv Roy would not approve.

After six years together, Kimberly Guilfoyle and Donald Trump Jr. called it quits in 2024. Since then, there's been more than a few times that Guilfoyle's outfits screamed revenge and this dress is definitely one of them. While the concept of the revenge dress is great in theory, it can sometimes makes the person wearing it look needy and desperate for attention. In the case of her red 2025 amFAR Gala outfit, which featured a dramatic leg slit and deep-v neckline, it's hard to not read the look as trying too hard.