Kimberly Guilfoyle's Inauguration Looks Are Some Of Her Most Questionable To Date

Donald Trump's second presidential term has brought mixed feelings across the board, but there's one thing many of us can agree on: The inauguration brought out some of the worst celebrity fashion looks we've ever seen. Conservative news personality Kimberly Guilfoyle — who never misses an opportunity to make a statement — may have led the charge with fashion fails at the historic event. To mark her new role as American Ambassador to Greece, the former news commentator wore outfits that seemed determined to make as much noise as the appointment itself.  

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At this point, Guilfoyle's fashion faux pas are almost as reliable as her enthusiasm for the spotlight. At Trump's pre-inauguration celebration, she donned a flashy, floor-length fringe flapper dress that was hardly befitting a political event. Its pantomime essence gave onlookers less couture, and more costume. But this was far from the only fashion faux pas Guilfoyle committed over the weekend. 

The flapper dress was a failed attempt at high fashion

Coco Chanel once famously warned: "Before you leave the house, look in the mirror and remove one accessory." We wish Guilfoyle had heeded this advice. Instead, she broke the cardinal rule of accessorizing: pairing a gaudy, oversized necklace (a crystal-studded cross, no less) with dangling earrings. Her signature heavy black eye makeup struck the final blow; it clashed uncomfortably with her disjointed attempt at sophistication. Unfortunately, this look was more flopper than flapper.

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Her dress at the Hispanic Inaugural Ball turned heads for all the wrong reasons

At the Official Hispanic Inaugural Ball on January 18, Kimberly Guilfoyle was papped alongside Cuban-born fashion designer Oscar Garcia-Lopez, best known for winning the first and only season of "Project Runway: Under the Gunn." The irony is not lost on us that standing next to a fashion designer couldn't save her from looking like a walking fashion disaster.

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For this event, the former Fox News presenter stepped out in a black gown bursting with colorful floral embroidery. The off-the-shoulder neckline made for a deliberately busty look, whilst the figure-hugging fit failed to hit the right sartorial notes. The dress left little to the imagination, and even less to praise.

Her penchant for revealing dresses has reportedly caused friction in her personal life. According to People, some reports suggest that Donald Trump Jr.'s alleged dissatisfaction with Guilfoyle's controversial fashion choices was one of the reasons he strayed towards his rumored mistresses. This look may have been intended to impress, but instead, it landed squarely in the realm of overdone.

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Kimberly Guilfoyle wore a strange pantsuit ensemble

On the day of Donald Trump's inauguration, Guilfoyle took a stroll up Capitol Hill arm-in-arm with her son, Ronan Anthony, from her short-lived second marriage to businessman Eric Villency. With her ex, Donald Trump Jr., and his new girlfriend, Bettina Anderson, spotted at an inauguration party together, you might have expected Guilfoyle to lean into some strategic revenge dressing. Instead, her outfit — a white suit paired with a matching pussy-bow blouse — quickly crumbled under the weight of its own mismatched components.

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The entire ensemble felt off balance. The suit itself, though sharply tailored, became a visual casualty of clashing choices. The pristine white was overwhelmed both in color and in shape by the bulky black coat she layered over it. Its fur shoulder pads exacerbated the essence with their odd silhouette. What's more, the beige of her pointed court heels felt random and ill-considered against the black and white. Pantsuits were once a staple of power dressing, but Guilfoyle's iteration seemed more like power fumbling.

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