Don Jr.'s Girlfriend Bettina Anderson's Fashion Fail Looks Ripped From Kai Trump's Closet

Don Jr.'s pre-Super Bowl appearance proves one thing — Kimberly Guilfoyle and Bettina Anderson have more in common than anyone realized. Sure, their styles are polar opposites, but both sit at the extreme ends of fashion. Guilfoyle dresses like every event is a Las Vegas after-party, and Anderson showed up at the Fanatics pre-Super Bowl 2025 party looking like she raided a teenager's closet.

The new couple attended the 2025 Fanatics party ahead of the Super Bowl on Monday. And while the first son looked every bit his age in a black shirt and graying hair, Bettina seemed determined to look even younger, pairing a denim jacket with a denim crop top, a loosely hanging belt, and what appears to be a brown crossbody bag. It was giving Teen Vogue inspo page style.

It's not the first time the Palm Beach socialite has been accused of dressing like a child. She recently drew criticism on Facebook for wearing a short, long-sleeved pink ball gown back in 2020. "A little old for this look," one commenter pointed out. But Anderson clearly doesn't care what fashion critics think, so we have to wonder if she'll rock light-up sneakers next.

Although Don Jr.'s friends might not be fans of his new girlfriend, he and Bettina Anderson seem to be going strong. Anderson is already posting MAGA footwear, trying to outshine Kimberly Guilfoyle by sucking up to Melania Trump, and even cozying up to Don Jr.'s former stepmother. Insiders also say they see the couple potentially lasting (via People). Bettina Anderson has notably never been married (at least, publicly), and a Trump-Anderson wedding would definitely be Palm Beach's wedding of the year.

However, there is one roadblock to this happily-ever-after: Donald Trump. Don Jr. is notorious for needing his father's approval. He reportedly married Vanessa after Donald introduced them and ended his alleged affair with Aubrey O'Day because Daddy Dearest didn't approve. Now, it seems Don Jr. could fail to earn Trump's approval again — thanks to Bettina's past social media posts. She previously supported Black Lives Matter, mocked the 2020 election, and even posed wearing a face mask during the coronavirus pandemic. On the plus side, if Anderson has her eye on a ring, she has only one task: win Donald Trump over.