The Tacky Outfit Kimberly Guilfoyle Wore That We'll Never Forget

Kimberly Guilfoyle has certainly become a memorable figure, and not necessarily for the best reasons. Her fashion and taste have become hot topics, though not always in positive ways. She's become one of the go-to examples of the latest plastic surgery trend, "Mar-A-Lago Face," a particular aesthetic that has taken over many of President Donald Trump's followers. It's not exactly a compliment; the look, which Guilfoyle seems to constantly cultivate, is one of unapologetically fake work, with exaggerated lips, excessively bronze spray tans, and makeup that's thick and heavy. She goes hard with that eye liner. 

She hasn't always looked this way; in fact, Guilfoyle's transformation over the years is a sight to see. The biggest shift in her taste and outward appearance came when she hitched her wagon to the MAGA horse. Guilfoyle's style became more flashy, her taste more risqué, leaning hard into sequins, glitter, platform heels, and body-con dresses. As if in a culmination of these sartorial choices, Guilfoyle's Inauguration looks were some of her most questionable outfits to date. It doesn't end there. Speaking of this time period, one of Guilfoyle's most unusual (or tacky) choices of all came in the form of a long, white flapper dress that she wore on January 19, 2025, right before Trump's inauguration ceremony. The look marked a distinct departure from her Fox News style, or her previous political-adjacent getups. 

At a pre-inauguration celebration for President Donald Trump on January 19, 2025 at the National Building Museum, Kimberly Guilfoyle arrived in a sequin, white column dress with a thigh-high slit and pale blue flapper ruffles that went all the way to the ground. She paired this with a large cross around her neck. Typical of her usual style (what we now refer to as that dreaded "Mar-A-Lago Face"), Guilfoyle wore her long hair parted down the middle in big curls, and rocked heavy, impactful makeup. It was a lot of what we're used to with her, but with the added style of the flouncy, unexpected flapper dress.

To make things even more awkward, Guilfoyle was the ex-girlfriend at the party. She had previously been engaged to Don Trump, Jr., but that fizzled around the end of 2024. Since their engagement, Don Jr. has started dating socialite Bettina Anderson, who attended the pre-inauguration dinner as well, and looked sleek in a black halter dress. That could not have been an easy or comfortable situation for either party. But Don Jr. and Guilfoyle allegedly had a fairly amicable split; plus, she was made ambassador to Greece in December 2024, so she's clearly not going anywhere during Trump's presidency, despite her fizzled relationship with his son. Since she's not leaving the MAGA circle any time soon, we can only hope that Guilfoyle ditched the frills, flounces, and flapper style soon.