Kimberly Guilfoyle's Most Inappropriate Outfits At Mar-A-Lago

Back in the good old days, Kimberly Guilfoyle was a near-permanent fixture at Mar-a-Lago, popping up at holiday celebrations, family dinners, charity extravaganzas, and even on the golf course from time to time. However, sadly, following Guilfoyle and Donald Trump Jr.'s messy breakup, she rarely graces the gaudy halls of the Florida estate now. Still, even though she may be gone, Guilfoyle's spectacular array of tasteless plunging dresses and atrocious attire she's worn to Mar-a-Lago over the years ensures she will never be forgotten.

There is absolutely no doubt that Guilfoyle has a very unique sense of style. It's like the "Real Housewives," combined with a hefty dose of stripteuse and a pinch of "Shahs of Sunset," with the occasional belly dancer homage thrown into the mix for good measure. 

Guilfoyle's inappropriate outfits reportedly landed her on Donald Trump's bad list, leading to the beginning of the end for #Donberly. To ensure an easy and painless extraction from the MAGA in-crowd, Donald nominated his son's ex-fiancée to be the ambassador to Greece in December 2024 — a position that presumably doesn't require any formal or modest clothing to be worn, fitting perfectly with Guilfoyle's flesh-flashing, busty outfits. But before she heads off overseas, we're checking out some of the former news host's most unseemly outfits she's worn at Mar-a-Lago. From the wildly inappropriate dress Guilfoyle wore to a charity event to the plethora of thigh-skimming, boob-baring frocks, each one is worthy of a place in fashion history.

Kimberly Guilfoyle looked like a gothic pageant princess as she sashayed her way down the staircase at Mar-a-Lago in early 2025. Donald Trump Jr.'s former wife-to-be was all toothy smiles, never taking her eye off the camera as she swished the full and flowing feathery skirt that was attached to her exceedingly low-cut and material-free lace top.

"Slay," Oscar Lopez, Guilfoyle's friend, captioned a video documenting the magnificent moment. Guilfoyle was accepting the Cigo Award, named after a brave K-9 that gave its life for its country. Her gown seemed rather inappropriate given the context, but, hey, that's how K-dawg rolls.

Kimberly Guilfoyle's skin-tight, glimmering, glittery gown gave even the gaudy and gilded Mar-a-Lago a run for its money when she attended a Donald Trump fundraiser in April 2024. "United in our mission, we march forward with determination," she captioned [in part] an Instagram photo of herself posing with Lara Trump.

Guilfoyle's thigh-skimming dress served almost as camouflage against the golden sunset behind her. Still, she definitely stood out from the crowd, which was pictured milling around behind her, clad in clothes way more appropriate for a sunset soiree.

Kimberly Guilfoyle's keynote speech in support of Arizona Congressman Abraham Hamadeh at Mar-a-Lago in March 2024 was undoubtedly memorable. In fact, it will likely be seared into the memory of attendees forever. Unfortunately, though, it wasn't Guilfoyle's rousing speech that was indelible; instead, it was the hot mesh black dress in which she was clad (well, semi-clad, anyway).

Guilfoyle's outfit took inappropriate to a whole new level with the skin-tight black Lycra number that had a deep-cleavage black mesh open panel that barely covered her nipples and a black mesh side panel split so high it reached her hip.

Kimberly Guilfoyle looked fit for prom night in December 2023. Instead, however, she was celebrating the holidays at Mar-a-Lago with then-fiancé Donald Trump Jr.

Shockingly, given that her baby doll disaster looked like it was plucked from the railings of a shady 18+-only back-alley store, the diamante-edged crepe mini dress was actually by Portrait, with a retail price of $249. That goes to show that you really can't put a price on inappropriate attire, especially when it appears that Guilfoyle's outfit was likely an "influencer" freebie — given that she tagged all the designers in her Instagram post.

Kimberly Guilfoyle proved once again in March 2021 that her inappropriate outfits don't come cheap. She posted a picture on Instagram, showing herself sandwiched between Donald Trump Jr. and Donald Trump, with Texas Congressman Ronny Jackson and his wife, Jane, all giving the obligatory MAGA top brass thumbs up.

Donald was clad in his usual go-to, ill-fitting, boxy blue suit, while Jr. matched his attire (minus the tie). Still, Guilfoyle went all out, pouring herself into a skintight $1,780 Missoni paneled metallic crochet-knit midi dress that looked two sizes too small, stretching the V-neck tightly across her chest and revealing one heck of a lot of cleavage.