The Outdated & Inappropriate Outfit Kimberly Guilfoyle Should've Kept In The Closet
Thanks to an impressive level of consistency, Kimberly Guilfoyle is known for her inappropriate outfits. You probably remember the chainmail club-style black dress she wore to a political event and proudly posted on Instagram, and you might have also seen Kimberly Guilfoyle's risqué red gala dress. However, one look she'll never live down was a merger of the two worst types of outfits: inappropriate and outdated.
In August 2025, after receiving an invite to an all-white party to celebrate a friend's anniversary, Guilfoyle combined her usual tacky dress sense with one of the fall dress trends that are totally outdated: cutouts. The dress was short, cleavage baring, and frilly, which in itself, was overwhelming. But paired with side cutouts, it was an impressive level of tastelessness. Sure, friend gatherings are not exactly strict on dress codes, but wearing that to someone else's anniversary party seemed like a step too far, especially when you consider what the guests in the background of her photos had on.
Guilfoyle finished the outfit with her signature style markers — obviously fake hair extensions and too-heavy makeup that was incredibly dark around the eyes. On one hand, we concede that everyone has a right to choose their own style, but on the other, staying appropriate and up-to-date with current styles is a huge part of fashion. And considering just how out-there the U.S. ambassador to Greece is with her outfits, there's no denying she dresses to be noticed.
Kimberly Guilfoyle's tacky sense of style has become infamous outside the U.S.
In 2025, Kimberly Guilfoyle officially became the U.S. ambassador to Greece amid worries that she wouldn't be able to keep up with the expected fashion rules that U.S. diplomats follow. Some of these rules include avoiding short skirts, cleavage-baring outfits, and other similar ensembles in order to keep the focus on the job at hand. So, how has Guilfoyle kept up with these guidelines? We'll give you a hint: not very well.
A January 2026 piece from The New York Times revealed that Kimberly Guilfoyle's fashion mishaps have followed her all the way to Greece. From sheer dresses to overly tight outfits and revealing ensembles, the entire country is reportedly already aware of her interesting fashion tastes. In fact, some of Kimberly Guilfoyle's teeny-tiny outfits that should have stayed in the closet were worn after she moved to Greece and began her ambassador duties.
But here's the thing: revealing outfits have no business at political events and are completely inappropriate. In many cases, they take the spotlight off of a politician's duties, and onto what they're wearing, which is disrespectful to the people they are meant to represent. There's nothing wrong with showing off one's personal style through fashion, but it's important to learn how to respectfully put a creative spin on corporate wear. Unfortunately, when it comes to Guilfoyle, we're not holding our breath.