Whether you love or loathe Kimberly Guilfoyle's sense of style, there's almost no denying that the former First Lady of San Francisco turned prominent Republican figure doesn't exactly have the best sense of "time and place" when it comes to her fashion choices. Guilfoyle has sported some truly inappropriate outfits in her time, from walking around a carnival in high heels to wearing a skin-baring red dress to a charity gala . Even some of Guilfoyle's own associates have allegedly taken issue with this trend, with an anonymous political source telling People in 2024, "The tight dresses need to go and she has been told that." Guilfoyle always seems to be walking a fine line in that respect.

Guilfoyle revealed her yellow crochet dress in a "Throwback Thursday" Instagram post from A

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