The number of times we’ve seen Kimberly Guilfoyle in normal, event-appropriate clothes is extremely rare. She has a terrible habit of confusing fashion events for a nightclub and has donned the most tasteless outfits imaginable when campaigning for President Donald Trump. But lo and behold, Guilfoyle managed to defy expectations by dressing impeccably for Trump’s inauguration following a string of fashion missteps and faux pas. The ex-fiancee of Donald Trump Jr. looked surprisingly elegant and polished in an all-white suit — a far cry from her usual mini-dresses and flashy ensembles. She finished the look with a silk blouse, classic heels, and a small handbag, adding a black velvet coat for drama and warmth. “America is BACK!” Guilfoyle captioned a photo of her inauguration outfit as she stood next to her son, Ronan Anthony Villency, outside the White House. She added, “Celebrating with true patriots as President Trump leads us into the next chapter of greatness.”

Tasos Katopodis/Getty

Here’s what’s interesting about her inauguration ‘fit, though: while proper, Guilfoyle’s tailored suit looked like it could have been pulled straight out of Kamala Harris’ closet given the latter’s well-documented penchant for power suits. In fact, five years ago, Harris wore a nearly identical ensemble — from the ribbon top down to the heels — during her victory speech as the first female African American to be elected vice president in 2020. Who would’ve guessed these two would ever have a twinning moment? Certainly not us. Anyway, Guilfoyle being Guilfoyle, she later traded her power suit for a busty blue floor-length dress at the Starlight Ball filled with MAGA patriots. She also showed some skin in a black floral gown at the Hispanic Inaugural Ball, where she shared the stage with Don Jr. Oh well. Guess she wanted to catch her ex’s eye.

Ever since the inauguration, Kimberly Guilfoyle seems to have dialed back her party girl style and embraced a more elevated and sophisticated wardrobe. For instance, while celebrating Greek Independence Day with Donald Trump, Guilfoyle — who was appointed the U.S. ambassador to Greece by the president — arrived at the White House in a bright red pantsuit paired with a white long-sleeved blouse. For her confirmation hearing as Greece ambassador in July 2025, the former Fox News anchor also looked surprisingly well-dressed in a black blazer jacket and trousers with the same silk blouse. But old habits die hard, it seems: Guilfoyle still hasn’t fully retired the tacky dresses and busty ball gowns that have long been her trademark. At a Mar-A-Lago charity event in March 2025, the Trump loyalist sported a wildly inappropriate dress with a deep plunging neckline that highlighted her decolletage. And, at the amfAR Gala Cannes in May 2025, she also stunned in a daring red gown with just enough fabric to cover her tatas. Shocking!

In the wake of her breakup with Donald Trump Jr., sources reveal that the first son had grown increasingly uncomfortable with Guilfoyle’s skimpy wardrobe toward the end of their relationship. “The tight dresses need to go and she [Kimberly] has been told that,” a source informed People in December 2024. They added that Junior’s new girlfriend, model Bettina Anderson, fits in better with the family’s image, both socially and style-wise. “Don Jr has always wanted to look good in his father’s eyes,” the insider pointed out. “Someone like Bettina, who is and has been a model, and is in Waspy circles of Palm Beach is something that would impress [his father],” they concluded.