Don Jr.'s Girlfriend Posts Humblebrag That's A Twist Of The Knife To Kimberly Guilfoyle

Donald Trump Jr. and Bettina Anderson's relationship has a messy timeline. After Trump Jr.'s engagement to Kimberly Guilfoyle was over, it took a long time before they publicly announced their split. Around this time, one insider theorized Guilfoyle's fashion sensibilities played a role in the breakup. "Don Jr. has been telling people for months that Kim is so uptight and always dresses so professionally in these kinds of dresses and high heels, and never looks relaxed or casual," they explained to People in December 2024. "The tight dresses need to go and she has been told that." Unfortunately for Guilfoyle, even when she tried to look professional, it often resulted in a fashion fail. In contrast, Anderson recently touted a style win in a September 2025 Instagram story, reposting a photo and quote from a recent Forbes article.

Nicole Prudot D' Avingy, Anderson's hair color artist, first disseminated the news, and the referenced article oozed praise for Anderson's sartorial choices. Perhaps as a nod to Trump Jr.'s criticism, it included one of Anderson's more casual, sneakers-based 'fits, which was worlds away from Guilfoyle's preferred styles. It's especially difficult imagine Guilfoyle in athletic footwear, since her shoe collection is dominated by high heels.

Even before Anderson twisted the knife, the article included a veiled dig at Guilfoyle. "[Anderson] often chooses sleek, tailored silhouettes reminiscent of the quiet luxury trend in lieu of garish colors or loud displays as we've seen from past paramours of the political family," remarked journalist Tanya Akim.

The September 2025 Forbes article isn't the first time Bettina Anderson has been complimented for her sense of style. "'Her choices so far demonstrate a willingness to take risks while maintaining a refined and polished aesthetic," Alisa Frederico, style director at Dressing Jane, informed the Daily Mail in January 2025. That same month, a Palm Beach Daily News photo spread included Donald Trump Jr.'s girlfriend rocking a variety of tailored coats and pantsuits. Even though it also showed Anderson wearing some shoulder-baring gowns, the piece seemed to take a subtle hit at Kimberly Guilfoyle by implying that Anderson's choices revealed a more appropriate amount of skin.

While Guilfoyle's long had a preference for revealing 'fits, she seems to have accentuated this part of her style since she split with Trump Jr. In May 2025, Guilfoyle's skin-baring gala dress included mesh panels that left most of her chest visible.

However, Anderson's increased time in the spotlight also creates opportunities for fashion missteps. Although the Forbes article commended her color choices, Anderson showed her similarities to Guilfoyle at the White House Easter Egg Roll by choosing a too-vibrant yellow coat that grabbed the spotlight. Way back in 2022, Anderson sported a mesh bodysuit that was on par with Guilfoyle's infamous see-through dress from 2019. However, one key difference is that Guilfoyle and Don Jr. were already a year into their relationship at that point, while Anderson had wore her revealing 'fit years before they began dating.