At first glance, Donald Trump Jr.’s ex-wife Vanessa Trump and ex-fiancee Kimberly Guilfoyle seem to have very little in common. One is a blonde, the other a brunette. One is heavily involved in politics, while the other prefers to stay out of the limelight. But aside from their connection to Don Jr., these two share one surprising trait — they both have a talent for rocking risqué, scandalous outfits. Guilfoyle, who was once engaged to marry Don Jr., is known to confuse fashion events for a nightclub with her gaudy fashion sense. Vanessa — although she tends to be more sophisticated — has worn some inappropriate outfits herself as well. Does this mean that Don Jr. has a certain “type” in women?

Not necessarily — at least, according to matchmaker and CEO of Exclusive Matchmaking Susan Trombetti. “I think it’s more about him being with bold, trendy, and glamorous women, and just who the women in his circle are,” Trombetti said in an exclusive Nicki Swift interview. “When it comes to clothing, even in the early 2000s, it used to be unacceptable to flash so much cleavage or be seen in clothes that weren’t so conservative. Today, anything goes.”

Take Jeff Bezos’ fiancée, Lauren Sanchez, for example. “Don Jr. has been exposed to celebrity and fashion circles where women don’t dress in sweaters and turtlenecks,” noted Trombetti. “[He] doesn’t seem to mind an edgier look and there is nothing wrong with that.” At this point, it’s less about Junior and more about these women asserting their right to dress as they wish and still being taken seriously. After all, regardless of how controversial their fashion choices are, “All of these women are serious,” stressed Trombetti. But what about Trump Jr.’s current girlfriend, Bettina Anderson?

As a model and socialite, Donald Trump Jr.’s new girlfriend, Bettina Anderson, knows how to keep things interesting when it comes to her style. A quick scroll through her Instagram page shows that she can effortlessly switch from classy and feminine to bold and daring, depending on the look she’s going for. Given that and her affluent background, it’s easy to see why she caught Don Jr.’s eye. “Bettina Anderson definitely aligns with Don Jr.’s previous choices [in women]. She is in the same social circle, she is bold, and cares about fashion,” said Susan Trombetti.

Unfortunately, while some might find her style more polished and sophisticated than that of Don Jr.’s exes, Anderson hasn’t completely dodged criticism over her fashion choices. Her denim ensemble at the Fanatics pre-Super Bowl 2025 party — where she and Don Jr. finally hard-launched their relationship (seen above) — is a prime example. “It’s just another fashion choice that all his exes have been critiqued for as well,” Trombetti explained. “Her style might be a little more conservative, but it still fits in with the fashion and glam that [Don Jr.] has grown accustomed to with the women in his life.”

If Anderson’s fashion sense reveals anything about Don Jr.’s preferences for women, it could be that he feels a sense of familiarity as her style mirrors someone else who’s close to him — his sister, Ivanka Trump. As a matchmaker and relationship expert, Trombetti thinks that this resemblance might be influencing Don Jr.’s attraction to Anderson without him even realizing it. She also claimed that this makes Anderson a natural fit for Don Jr., though whether he sees her as a potential lifelong partner at this point remains to be seen.