Kimberly Guilfoyle's Most Tasteless Outfits While Campaigning For Trump

Nothing is a certainty in life aside from death, taxes, and Kimberly Guilfoyle busting out with an inappropriate outfit. It doesn't matter what the event or occasion is; she has unbefitting attire for them all. Guilfoyle's risqué homecoming dance look from April 2024 comprised an exceedingly low-cut scoop neckline mini dress and rosette choker. While Guilfoyle's outfit she wore for her son's prom took improper to a whole new level. Still, Guilfoyle doesn't save unseemly styles solely for private occasions; she rocks tasteless ones while stumping for Donald Trump, too.

Guilfoyle has been a vocal and ferocious constant on the campaign trail, a fixture by Donald Trump Jr.'s side as they traverse the U.S.A., giving vitriolic, caustic, and ominous fiery speeches to adoring MAGA crowds. Guilfoyle becomes so het up on the podium that she sends the decibel counter off the scale. Something that hasn't gone unnoticed by late-night comedians. "We begin tonight with Kimberly Guilfoyle, who delivered the kind of monologue typically seen in a YouTube video of a maskless woman being kicked out of Trader Joe's," a cartoon anchor announced on the "Late Show" back in 2020.

And there's no arguing that Guilfoyle got decidedly amped up during her RNC speech. "Ladies and gentlemen, leaders and fighters for freedom and liberty and the American dream, the best is yet to come!" she screamed. Still, some pay more attention to Guilfoyle's tasteless outfits while she's campaigning rather than her fervid rhetoric. We're checking out some of the most ostentatious.

Guilfoyle's mesh chest and side split dress and gold platform heels

Kimberly Guilfoyle outdid even herself in the tasteless outfit stakes at Mar-a-Lago in March 2024. She was hosting a fundraising event in honor of Donald Trump-endorsed Republican U.S. House representative wannabe for Arizona's 8th District, Abraham Hamadeh. "The atmosphere buzzed with electric energy, fostering inspiring conversations and unforgettable moments. Thank you to the incredible @RealDonaldTrump for everything you do to make sure the right people are heard and supported," she captioned a video clip of the big day.

Well, one thing is definite: we can't comment on her speech, but Guilfoyle's outfit was certainly unforgettable. It comprised a black dress, slashed down to the navel with just a mesh panel to semi-save her modesty and a hip-high side split, also held together by mesh. She finished off the look with a pair of tasteful gold high-heeled platform sandals. Social media lit up with opinions on Guilfoyle's inappropriate attire. "What are you wearing — seriously. I am a Trump supporter," a confused commenter wrote. "Cover the girls up. We don't need to see them," another opined. "Someone call the fashion police!" a third quipped.

Meanwhile, despite — or perhaps because of — Guilfoyle's boob-baring ensemble, the event was a runaway success. The MAGA heavy hitters and go-getters were out in force, all batting for Hamadeh. Oh, and Rudy Giuliani was there, too, apparently.

Guilfoyle's TPAC boob baring blue dress

Kimberly Guilfoyle put her best assets forward at the 2024 Turning Point Action People's Convention in Detroit in June 2024. As a keynote speaker, Guilfoyle was there to fire up the crowds for the main event, her future father-in-law, Donald Trump. Fire them up she did, with a rousing, passionate, and fierce appeal to "All you lovers of liberty and freedom and the American dream!" Still, Guilfoyle kind of stole the show as she strode out onto the stage in a hip-hugging purple dress with a decidedly low neckline and a pearl choker.

"Fired up at @tpaction People's Convention in Detroit! Together, we're making America great again with powerful voices like @realdonaldtrump, @donaldjtrumpjr and @charliekirk1776. Ready to lead, ready to win in 2024! #MAGA #Patriot #TurningPointAction #LeadTheWay," Guilfoyle captioned a carousel of pics from the event that she posted on Instagram.

The Guardian described Turning Point USA as "a far-right youth group" that has become central to Donald's fundraising efforts and a pro at rallying the MAGA fanbase. Founder Charlie Kirk took to the stage along with Guilfoyle, Donald Trump Jr., and, of course, the leading man, Donald. Lara Trump, whose political career is growing stronger by the day, also entertained the crowds with a vow to prosecute anybody she deems as having cheated in an election,

Guilfoyle's AmericaFest thirsty thigh flasher and dominatrix shoes

Kimberly Guilfoyle's chest was on full display yet again at AmericaFest 2021. Still, she gave her thighs an airing, too, in a tiny black dress that left little to the imagination, especially when she was seated for interviews.

"Truly an honor to speak at the biggest event in the conservative movement, AmericaFest 2021! Thank you @charliekirk1776 and @laurenana for having me and for doing such an amazing job! [U.S. flag emoji] #AmericaFest2021 #AMFEST2021 #TurningPointUSA #TPUSA #Freedom," Guilfoyle captioned a carousel of photos from the event, including one of her sitting on a high stool, with the hem of her skirt skimming her behind, and a pair of dominatrix-style black high heels studded with spikes. The comments on Guilfoyle's Instagram post were suitably divisive and bizarre. "I love White Women that wears [sic] Pantyhose," one read." You should stick to wearing 'pants'... No offense. It's a better look for you," read another.

Meanwhile, AmericaFest is another event organized by the rising MAGA star Charlie Kirk and his fundraising group, Turning Point USA. Rolling Stone noted that the gathering of alt-right superstars is a beacon for anti-semites, Holocaust deniers, and white supremacists.

Guilfoyle's butt-skimming mini mini dress

Kimberly Guilfoyle went all out for the tasteless outfit she wore in London while campaigning for Donald Trump in June 2024. She was clad in a black and white knitted graphic mini dress that was so short it barely covered her butt. She topped off the look with a suitably tacky pair of white stiletto shoes. Still, despite Guilfoyle's outfit being tasteless, it was far from cheap. Her Balmain dress retails at a bargain $2,432.

Guilfoyle and Donald Trump Jr. were across the pond to host an exclusive meet-and-greet with campaign contributors. Tcket prices reportedly ranged from $10,000 to just be able to hang out in the political power couple's orbit to $50,000 to break bread with them. The private event, which was hosted at singer Holly Valance and her billionaire husband Nick Candy's Chelsea mansion, is believed to be the highest-grossing Trump fundraiser outside of the USA. It's estimated to have brought in in excess of $2 million.

Brexit king and far-right darling Nigel Farage was also in attendance. He apparently arrived solo, clasping a copy of the "Gospel of John" for some unfathomable reason. When reporters asked Farage if he was troubled about donating to a convicted felon's fundraiser, he dodged the question by pointing out that he can't vote in the U.S. election because he's British. Still, that hasn't stopped him from purportedly scoring a top job within Donald's campaign team.

Guilfoyle's black lace see-through corset catastrophe

Saving the best for last, Kimberly Guilfoyle really upped the tasteless outfit ante with the June 2024 ensemble she wore to meet with El Salvadoran President Nayib Bukele. Donald Trump Jr.'s fiancée flashed some serious flesh in a lace see-through corset top dress that flared out into a sheer net finish. Guilfoyle accessorized with a huge diamond cross necklace and something Don Jr. killed earlier — possibly — a black fur wrap.

"It was an honor to meet with El Salvador's President @NayibBukele. President @nayibbukele made history by becoming the first two-term President in El Salvador's history. His bold vision for the country will drastically improve the lives of his citizens," Guilfoyle captioned a carousel of pics showing her next to Don Jr., his chest puffed out in an ill-fitting tuxedo and wonky bow tie, and a couple of her dressed more modestly.

Bukele is a controversial figure, to say the least. After scoring a second term in office, The AP notes that he's gone from self-professed "world's coolest dictator" to his latest X, formerly Twitter, profile update as the "Philosopher King." And Bukele certainly keeps good company; his 6.2 million social media followers include Don Jr. and Manosphere President Anthony Dream Johnson.