4 Times Kimberly Guilfoyle Confused Fashion Events For A Nightclub

It's widely been speculated that her inappropriate outfits and party girl ways flushed Kimberly Guilfoyle's engagement to Donald Trump Jr. down the drain. "Don Jr. has been telling people for months that Kim is so uptight and always dresses so professionally in these kinds of dresses and high heels, and never looks relaxed or casual. The tight dresses need to go and she has been told that," a source told People in December 2024. In fact, there have only been a few rare times that we've seen Guilfoyle in normal clothes. 

Even at the most high-fashion events, Guilfoyle has leaned on her tired 2000s-era clubby style —think bodycon dresses, sky-high heels, and loads of thick and heavy makeup to boot. Let's roll the tape, shall we?

Kimberly Guilfoyle is no stranger to the fashion world. Way before she became the face of MAGA, Donald Trump Jr.'s high-profile ex, and the United States ambassador to Greece, a then-fresh-faced Guilfoyle was making her rounds at many high-profile fashion events all over New York City. Alas, even way back then, she wasn't exactly a fashion icon. 

Guilfoyle arrived at the fashion event wearing a metallic cheetah print piece by the high-end designer label Tibi. But as the iconic Countess Luann de Lesseps once waxed poetic, "Even Louis Vuitton makes mistakes." Sadly, Guilfoyle's chosen nightmare of a frock read like something straight out of "The Cheetah Girls" circa 2003. Alexa, play "Strut" by Cheetah Girls.

Lights, camera, action! Kimberly Guilfoyle was all smiles while seated front row with her then-boyfriend Donald Trump Jr. at the Zang Toi fashion show during New York Fashion Week in February 2019. Alas, the feel-good vibes proved short-lived when it became apparent that her sheer black Zang Toi ensemble adorned with a butterfly applique on one shoulder wasn't exactly flash photography friendly. Ruh-roh.

It should be noted, however, that this was not Guilfoyle's first rodeo with the Malaysian fashion designer. Over the years, Guilfoyle has been to many of Toi's shows and has worn many of his dresses. In fact, she was even backstage at his show in 2017. "This is what it looks like with all the outfits and all of the models getting ready," she gushed in a behind-the-scenes video. Perhaps next time, she can carve out some time backstage to check for any potential wardrobe malfunctions. 

Kimberly Guilfoyle was seated front and center at Emily Pantelides' Runway of Hope charity event on January 25. Guilfoyle attended the "where fashion meets philanthropy" soiree, whose mission is to end child exploitation, as a special guest. By all accounts, the runway event was a smashing success. "So many people to thank. Not enough words to express my heart. So for now, simply thank you for supporting Runway of Hope," Pantelides gushed in a post following the event.

Sadly, it appears Guilfoyle didn't get the memo when it came to dressing for the daytime fundraiser. As evidenced in photos posted by Pantelides and another attendee, Guilfoyle arrived at the event in a blinged-out mini dress that left very little to the imagination and a pair of metallic platform heels. Perhaps her only saving grace was the silver furry frock she wore over her shoulders. 

Orphans and animals and busty dresses, oh my! In March 2024, Kimberly Guilfoyle attended a charity event put on by Wine Women & Shoes in honor of — you guessed it — orphans and animals. "A great four days raising money for orphans and animals ... two integral parts of my life," Guilfoyle's gal pal Dr. Gina Gentry Loudon penned in part of an Instagram post along with several photos including one of herself, Guilfoyle, and two other unnamed women. (In case you missed it, Gina is the mother of Barron Trump's purported BFF Bo Loudon and spoiler alert: Gina dresses just as scandalously as Guilfoyle.) As evidenced in the photo, Guilfoyle chose an ethereal lavender and white dress. While the dress was more flowy than form-fitting, there was one area that it zeroed in on — Guilfoyle's chest. The plunging neckline plunged so far that it almost reached her naval. Woof!

In January, on the heels of her high-profile breakup from Donald Trump Jr., Guilfoyle posted a very busty throwback of the pic with the mom of Barron's best friend to her Instagram Story. She was careful, however, to give her ex's family a shoutout. "Thank you to ... the Trump family for always generously giving of their homes, their time, and their love!" Perhaps the throwback was also her way of reminding Don Jr. what he was missing.