Kimberly Guilfoyle's inappropriate outfits: 7 times the TV personality shocked with her fashion choices

Kimberly Guilfoyle's inappropriate outfits: 7 times the TV personality shocked with her fashion choices
Kimberly Guilfoyle has raised eyebrows with her fashion choices (Photo by Astrid Stawiarz/Getty Images for NYFW: The Shows) (Photo by Chip Somodevilla/Getty Images)

Kimberly Guilfoyle's most shocking fashion choices over the years

(Photo by Chip Somodevilla/Getty Images)(@kimberlyguilfoyle/Instagram)
Kimberly Guilfoyle is known for her eccentric fashion choices (Photo by Chip Somodevilla/Getty Images)(@kimberlyguilfoyle/Instagram)

Kimberly Guilfoyle's fashion choices often generate significant discussion and controversy. Here are some of the most inappropriate outfits she has worn in various public and political settings.

1. Tiffany Trump's wedding

(@Donald Trump Jr/Instagram)
Kimberly Guilfoyle attended Tiffany Trump's wedding in 2022 wearing an all-black dress with statement sleeves (@Donald Trump Jr/Instagram)

Kimberly Guilfoyle attended Tiffany Trump's wedding in 2022 wearing an all-black dress with statement sleeves. This choice starkly contrasted with the pastel shades worn by the rest of the bridal party. The contrast was so striking that Ivanka Trump cropped Guilfoyle out of a family photo she shared on Instagram, leading to widespread speculation and criticism online.

2. Republican National Convention 2020

Kimberly Guilfoyle walks on stage before pre-recording her address to the Republican National Convention at the Mellon Auditorium on August 24, 2020 in Washington, DC. The novel coronavirus pandemic has forced the Republican Party to move away from an in-person convention to a televised format, similar to the Democratic Party's convention a week earlier. (Photo by Chip Somodevilla/Getty Images)
Guilfoyle wore a flaming red, figure-hugging dress with a low neckline (Photo by Chip Somodevilla/Getty Images)

At the 2020 Republican National Convention, Guilfoyle wore a flaming red, figure-hugging dress with a low neckline. Her loud and forceful speech was matched by the bold outfit, which some commentators felt was distracting and inappropriate for the occasion. The New York Times even referred to her as the RNC's "woman in red."

3. Carnival in Louboutins

(@kimberlyguilfoyle/Instagram)
Guilfoyle attended a carnival at the Admirals Cove Club in Jupiter, Florida, wearing a sparkly Balmain dress and Louboutin heels.(@kimberlyguilfoyle/Instagram)

In December 2023, Guilfoyle attended a carnival at the Admirals Cove Club in Jupiter, Florida, wearing a sparkly Balmain dress and Louboutin heels. While her outfit was glamorous, it was impractical for a carnival setting, contrasting sharply with the casual attire of Donald Trump Jr and his children.

4. New York Fashion Week 2019

Kimberly Guilfoyle poses backstage for Zang Toi fashion show during New York Fashion Week: The Shows at Gallery II at Spring Studios on February 13, 2019 in New York City. (Photo by Theo Wargo/Getty Images for NYFW: The Shows)
Guilfoyle wore a dress with butterfly appliques on the sleeve at the New York Fashion Week in 2019. (Photo by Theo Wargo/Getty Images for NYFW: The Shows)

During New York Fashion Week in 2019, Guilfoyle wore a dress with butterfly appliques on the sleeve. The dress turned out to be too sheer under the paparazzi's flashing lights, revealing the stark outlines of her underwear, which led to considerable media attention.

5. Women for Trump rally 2020

(@kimberlyguilfoyle/Instagram)
Guilfoyle wore an all-pink sheath dress at the 2020 presidential campaign. (@kimberlyguilfoyle/Instagram)

At a Women For Trump event in Pennsylvania during the 2020 presidential campaign, Guilfoyle wore an all-pink sheath dress. The outfit matched the rally's signage but was criticized for being stereotypically feminine in a political context. This was particularly ironic given the extensive use of pink as a protest color following Donald Trump's inauguration.

6. Action People's Convention 2024

(@kimberlyguilfoyle/Instagram)
Guilfoyle wore a dark blue dress with a plunging neckline that extended to the ruched waistband (@kimberlyguilfoyle/Instagram)

At this convention, Guilfoyle wore a dark blue dress with a plunging neckline that extended to the ruched waistband. Paired with a simple pearl necklace, her dress left little to the imagination. While she aimed to energize the crowd with her speech, it was her daring outfit that became the focal point of the evening, drawing both criticism and attention.

7. Tigger Stavola Foundation

Kimberly Guilfoyle wore a mini-dress featuring a cut-out detail in the front, which gave it a bold and revealing look (@kimberlyguilfoyle/Instagram)
Kimberly Guilfoyle wore a mini-dress featuring a cut-out detail in the front, which gave it a bold and revealing look (@kimberlyguilfoyle/Instagram)

Kimberly Guilfoyle faced significant backlash after choosing to wear a skimpy dress -- a pink mini-dress featuring a cut-out detail in the front -- to a fundraising event aimed at fighting addiction. The event was organized by the Tigger Stavola Foundation, which focuses on spreading awareness and saving lives through drug prevention and education. Guilfoyle shared four photos from the event, which quickly garnered negative attention online. Critics argued that her choice of attire was inappropriate for the solemn nature of the event. 

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