Compared to other Republican media personalities, Kimberly Guilfoyle has arguably undergone one of the most drastic style transformations over the course of her career. Once known for her nerdy-chic looks, the former First Lady of San Francisco has leaned into an American beauty queen sense of style, complete with fashion and makeup mistakes we're begging Guilfoyle to ditch . From excessive makeup and hair extensions to club wear at formal events, the diplomat's sense of style has been the target of much criticism.

In 2024, Kimberly Guilfoyle wore a few outfits that completely missed the mark , but in 2025, things didn't seem to get any better. By analyzing Guilfoyle's 2025 outfits — sourced from her own and others' social media, as well as major public events — we evaluated her best

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