Kimberly Guilfoyle is known for taking fashion risks, but it seems her affinity for ultra- glitzy, high-glam ensembles have unfortunately landed her squarely on the fashion hall-of-shame. In October 2025, while attending The Hellenic Initiative’s (THI) London Gala, alongside distinguished leaders of the Greek diaspora, the political commentator committed yet another unforgettable style faux pas. Decked in a David Koma Macramé red dress, she delivered an overly garish look with too many outdated trends.
For one, the tomato-red hue, paired with matching red accessories, were among color palettes named in outdated trends to ditch in fall 2025. The head-to-toe netted appearance and fit-and-flare shape, meanwhile, is reminiscent of styles that were everywhere back in 2010. Then there was Guilfoyle’s Tiffany & Co. Red Satin Mini Handbag — a discontinued item that’s only available through luxury resale and vintage marketplaces.
Of course, the likes of Kimberly Guilfoyle wouldn’t be rocking just any off-the-rack find. This David Koma Macramé Maxi Dress, featuring intricate textile embroidery, will take you back $3000. The high-neck, long-sleeve design with a fluted hem includes a separate red under-layer and a concealed back zip fastening. It’s tailored for a slim fit that accentuates curves, creating a flattering silhouette as it cascades into a flared midi-length skirt. While Guilfoyle certainly nailed the fit, she unfortunately checked several boxes on the fashion don’ts list.
Guilfoyle is a repeat offender of outdated trends
It seems the former prosecutor’s fascination with high-end designs has blinded her fashion sense when it comes to trendier styles. Guilfoyle’s most inappropriate dresses have reflected a palette that blends fairytale-princess gowns with racy disco tech attire — not the most suitable dress code for the President Trump-appointed U.S. Ambassador to Greece.
Proving she is a repeat offender of outdated trends, Guilfoyle wore a pink Rebecca Vallance ‘Karina Puff Sleeve Mini Dress’ to a drug education fundraiser in June 2024. The dress not only looked pretty dated but also inappropriate for the occasion, featuring elaborate short puffy sleeves and crystal-embellished double cutouts at the neckline that revealed her cleavage. Guilfoyle paired the mini dress with sparkly, double-platform heels, creating a complete look that took us back to the ’90s. A month earlier, she unveiled a similar fairytale-inspired ensemble, wearing a Jenna Mini Dress (also by Rebecca Vallance) with a seashell bustier design.
Besides the many outdated fashion trends Guilfoyle can’t seem to stay away from, her hair and makeup choices have added another layer to her old-fashioned look. As recently as 2025, she has been photographed wearing dramatic smoky eye makeup, darkened brows, and long, volumized hair, often styled in a bouffant reminiscent of the ’60s — a look people are now calling her out on, while urging her to get a makeover. “Please offer this woman a [s]tylist and a makeover. The hair looks awful and the way overdone makeup really ages her…” a commenter wrote on a 2025 Daily Mail article. Another observer added, “She needs to decrease the eyeliner and shadow. Maybe the foundation too…”
