Kimberly Guilfoyle's Inappropriate Hamptons Outfit Didn't Do Her Any Favors

If there's one thing we know about Kimberly Guilfoyle's wardrobe, it's that chances are whatever she puts on won't be the appropriate attire for the function she's attending. Case in point? Kimberly Guilfoyle's most inappropriate outfits so far. Whether it was she was Gavin Newsom's wife, Donald Trump Jr.'s fiancée, or President Donald Trump's pick to be the United States' ambassador to Greece, the former prosecutor has proven that she loves to show up to events with far too much skin showing.

Take, for instance, the Social Life Magazine's 2018 Memorial Day Issue and 15th birthday celebration in the Hamptons. Guilfoyle opted for a pair of low-waisted, cherry-red capris and a cropped, polka-dotted blouse. She paired the look with hoop earrings, a statement necklace, and white-and-black pumps. It seems as though she was going for a "sailed away" Hamptons vibe, but all that translated was Boo Boo the Fool.

To start, the silhouette was abysmally poor. The flowy, long-sleeved top, being cropped right above her belly button, made her proportions incohesive. The waistline of the pants was also not intended to be worn with the midriff showing, as they cut into her lower abdomen and sagged at the crotch. None of the colors Guilfoyle was wearing went together, but what truly made this look inappropriate was that it was too casual for a media party.

Kimberly Guilfoyle's risqué gala outfit that pushed boundaries (even for her) shows that she loves a scantily clad silhouette. While some of her choices might have been fashionable, very few were the right (or even the appropriate) look for the function. Her ensemble for the Social Life Magazine's 15th birthday party in 2018 was just the beginning of this trend, and that wasn't even her worst fumble.

Kimberly Guilfoyle was rocking her classic, outdated smokey eyeliner look to New York Fashion Week in 2019, and opted for a black knee-length bodycon dress with embellishments around one of the sleeves. She paired the garment with matching black pumps, but when flash photography was used to take her picture, there was nearly nothing left to the imagination. To make matters worse, she decided to step out sans bra. Though it wasn't inherently Guilfoyle's fault, a quick flash test would've come in handy before she hit the town.

Fast forward to March 2024, and Guilfoyle was hosting a fundraiser for Abraham Hamadeh's Congressional Campaign at Mar-a-Lago. What might you wear to an event like that? Perhaps a power pantsuit or a sophisticated cocktail dress. Instead, Guilfoyle wore yet another figure-hugging black gown that had a plunging neckline and a high slit that was merely covered by mesh, see-through fabric. Perhaps Guilfoyle's revealing closet will be better suited for the Greek summer.