Whether you know her from Fox News or as the fiancée of Donald Trump Jr., there is no denying that Kimberly Guilfoyle is a woman who is hard to forget. Thanks to her bold presence and unwavering confidence, the beauty has managed to rise to even more popularity as a part of the Trump family. However, just like Ivanka Trump — whose most inappropriate outfits we surely won’t forget — Guilfoyle has also had her fair share of fashion mistakes.
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From flash photography ruining her big red-carpet moment on multiple occasions to her outright refusal to let go of noughties trends — even though Y2K fashion is back and we love styling it in 2024 — here are some of Kimberly Guilfoyle’s biggest fashion mishaps that prove even stylish women like her can have a really bad fashion day.
Not testing if an outfit is flash-photography proof is a fashion faux pas Kimberly Guilfoyle can’t afford
Anyone who gets photographed a lot knows that outfits often look very different in person and in photography. While this usually means that a piece just doesn’t look as pretty in a photo — it can also mean that its color changes or it ends up looking see-through with flash photography. And the latter is exactly what happened to Kimberly Guilfoyle when she attended New York Fashion Week in 2019. The television news personality showed up at the Zang Toi fashion show in a knee-length black dress with butterfly embellishments around one sleeve. Even though the clothing piece actually sounds great in theory, in practice, flash photography made the black fabric a bit more see-through than intended.
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Kimberly Guilfoyle should know that red pants and a crop top aren’t event attire
Casual fashion for industry events was a big part of the early aughts, but as time moved on, celebs have learned that there is a time and place to look casual, and on a red carpet or in front of a media wall usually aren’t it. In 2018, Kimberly Guilfoyle attended the celebration of Social Life Magazine’s Memorial Day Issue as well as their 15th birthday in Bridgehampton, New York. It may not have been the Academy Awards, but red pants and a crop top still seem a bit too casual if you ask us. But hey, we can’t blame her for wanting to show off those abs!
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Kimberly Guilfoyle seems to often be guilty of slightly see-through pieces
In 2017, Kimberly Guilfoyle attended Zang Toi’s fashion show at New York Fashion Week, and similar to her look in 2019 — the dress she was wearing wasn’t really flash-photography-proof. Luckily, while the black material was rather see-through, the white flower and butterfly pattern on it helped distract from the fashion faux pas a little. Unfortunately for the former prosecutor, some skin was still unintentionally on display — the internet never forgets, and neither do we.
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A bright neon peplum dress is a bold choice at a Republican event for Kimberly Guilfoyle
When Kimberly Guilfoyle was attending a campaign event for Donald Trump in Nevada in 2020, the former Fox News personality decided that a neon shade of mint would be perfect for the occasion, despite it being worlds away from the Republican-favored red. Now, to make matters worse, she opted for a peplum dress, reminding millennials across the globe why corporate fashion at the club (or the campaign trail) was an atrocious trend we hope to never see again.
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Kimberly Guilfoyle wore this Kardashian-like piece in 2024, not 2014
When Kimberly Guilfoyle was spotted leaving a restaurant in London, England, in June 2024, we couldn’t help but notice that the minidress she was wearing was particularly similar to the early-to-mid 2010s trend set by the KarJenners. For those who need a reminder, the era was particularly marked by the Kardashian-Jenners wearing ultra-short, long-sleeved dresses with intricate detailing, often by high-end designers like Balmain. Now, we don’t have anything against the particular style, but seeing Guilfoyle wear it 10 years later makes it seem a bit outdated.
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Shiny stockings can make or break an outfit — and in this case, they broke Kimberly Guilfoyle’s
A fashion faux pas that no one in the spotlight can really afford is shiny stockings — unless they are intentional, of course. However, we fear that when Kimberly Guilfoyle attended a screening of “Elysium” in New York City in 2013, she probably wasn’t aware of the fact that flash photography would switch the spotlight from her classic red dress to her shiny legs. Once again, the star didn’t test her look properly before heading to the event.
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We hope that colorful leopard print is something Kimberly Guilfoyle doesn’t have in her closet anymore
Even though 2000s fashion has had its resurgance over the past couple of years, one trend from the era we hope won’t come back anytime soon is colorful animal print. We don’t hate it completely, but we’re aware of how difficult it is to pull off, so it often misses the mark. Case in point: the messy minidress Kimberly Guilfoyle wore at the Tibi show at New York Fashion Week in 2011. Trying to blend hot-pink animal print, ultra-short length, a satin finish, and sheer tights, this look was all over the place. Now, if you want to see more fashion blunders from the Trump women, check out the outdated outfits Tiffany Trump has been caught wearing.
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