Kimberly Guilfoyle's Bustiest Look Was So See-Through We Had To Cover Our Eyes

Kimberly Guilfoyle's transformation over the years has been nothing short of jaw-dropping. The former Fox News host grew up in a modest, middle-class family and proceeded to enjoy careers in both law and journalism before being appointed to her latest position as the U.S. ambassador to Greece. Along the way, of course, Guilfoyle also came this close to becoming the daughter-in-law of President Donald Trump. Unfortunately, despite her many accomplishments, she seems destined to be remembered for two things: Being publicly jilted by ex-fiancé Donald Trump Jr., and being the center of attention for all the wrong reasons. Guilfoyle's inappropriate outfits have become her signature look, much to the pleasure of some fans and the embarrassment of many others. 

The MAGA loyalist can always be counted on to show up to any event in an ensemble that's either super low-cut, thigh-baring, or both. Tight miniskirts and dresses with plunging necklines are her specialty, all accessorized by heels high enough to make a podiatrist wince. We can't say for sure whether she's desperate to be noticed or simply making a statement about midlife sexiness, but the Trump staffer shows no indication of changing her style to suit her critics any time soon. 

Case in point: The skin-baring red dress that Guilfoyle wore to the amFAR gala in Cannes in June 2025. It featured just enough satin and lace to stay (barely) within the realm of decency. However, on at least one occasion, the former prosecutor revealed too much without actually meaning to. In one such instance, a crucial misjudgment on her part resulted in a peekaboo moment that still has us blushing on Guilfoyle's behalf.

As a former model and well-connected media personality, Kimberly Guilfoyle gets tons of invites to major social events, among them New York Fashion Week, which she attended in 2019 with her then-boyfriend Donald Trump Jr. Appearing at a show promoting designer Zang Toi's latest line, Guilfoyle wore what appeared to be a simple black mesh dress with an appliquéd butterfly detail on one shoulder strap. She might have gone relatively unnoticed if she hadn't posed for a round of photos on both the floor and the red carpet. The flash illuminated everything underneath, in particular her white sticky bra. Ironically, the cut of the dress was otherwise more modest than the U.S. ambassador to Greece normally wears, and for once Guilfoyle's overdone hair extensions stayed at home too.

Still, it's a pretty safe assumption that she didn't plan to have her, um, natural assets on display. Nowadays, of course, the former Fox News host is all about being risqué, typically choosing cleavage-baring cuts and ignoring the ribbing she gets about it on social media afterwards. Humorist Paul Rudnick, in particular, loves to poke fun at her fashion choices on X, formerly known as Twitter. 

One typical post: "Kimberly Guilfoyle's style icons are Real Housewife Teresa Giudice and Leona Helmsley. The look says, 'Jail time, lipstick and lies — mob wife with a splash of Cruella. Arrested at Olive Garden under the name Jillian St. Clair. No character witnesses.'" Still, the Trump diplomatic appointee has learned her lesson in one area of fashion: She may still have that white undergarment in her dresser, but she hasn't shared it with the public since her oopsie moment.