Kimberly Guilfoyle's Crochet Dress Was A Fashion Faux Pas Waiting To Happen

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 August 2025, in which she reminisced about attending her friends' 10th wedding anniversary celebration in Islamorada, Florida sometime prior. First of all, crochet tends to be rather see-through, meaning the risk of a wardrobe malfunction may already outweigh any potential style points here. We suppose that one benefit of having a dress like that is that it would breathe relatively well, but crochet is also warm and heavy, so even if there's a nice sea breeze going, wearing one in Florida sounds like it would be downright miserable, especially given the fact that Guilfoyle paired it with a denim jacket.

Mirroring the carnival incident, Kimberly Guilfoyle rounded out her crochet-centric look with what appears to be a pair of open-toed shoes, thus adding a cherry on top (or on bottom, we suppose) of what had to have already been a painfully uncomfortable outfit. We can certainly appreciate prioritizing fashion over practicality every once in a while, but more often than not, you'll be thanking yourself for choosing a pair of sensible shoes.

Guilfoyle's style transformation has apparently led her to a place where she chooses her outfits based on what she think would be the most photo-worthy, not what would be the most appropriate for the situation at hand. What's more, excess seems to be her middle name. (Her middle name is actually Ann, but you know what we mean.) Putting most sneakerheads to shame, Guilfoyle confessed in a 2017 interview with Us Weekly that she likely owned around 500 pairs of shoes.

Similarly, Guilfoyle's tendency to compromise functionality in the name of flashiness isn't exactly a recent development, either. Speaking to Footwear News in December 2016 ahead of New Year's Eve at Times Square, Guilfoyle made it clear that she believed surviving the New York nighttime winter air and wearing an outfit she liked were of relatively equal importance. "One thing you have to prepare for is being insulated but fashion is a priority," she said.