Don Jr.'s Ex Vanessa Trump Has Worn Some Inappropriate Outfits

As the iconic Countess Luann De Lesseps famously crooned, "Money can't buy you class. Elegance is learned." Perhaps no one knows that better than Donald Trump Jr.'s ex-wife, Vanessa Trump. As reported by Page Six, Vanessa and her family fell into "life-changing" millions in the most unusual way. (Hint, hint: It's not about the pasta. It's about the sauce — Rao's marinara sauce, to be exact.) 

While one might assume that Vanessa's deep pockets afford her an excellent sense of style, sadly, nothing could be further from the truth. While Vanessa's look has changed drastically since her divorce from Don Jr., she continuously misses the mark as it relates to her fashion lewks. Over the years, the mother of five has really taken some serious heat for her fashion faux pas and outfits that just didn't work.

Charity, but make it fashion? Unfortunately, it appears that Vanessa Trump pushed the envelope just a little too hard at Operation Smile's Gala "Smile Collection" Couture Event in May 2004. No doubt, the dress was red hot, but not for the reasons one might imagine. Think: a chaotic red and white print, a dangerously tight fabric, thin straps that criss-crossed at her collarbones, and a plunging neckline that left very little to the imagination. Now that we think of it, the garment is eerily reminiscent of the wildly inappropriate dress Kimberly Guilfoyle donned at Trump National Golf Club in November 2024.

Unfortunately, Vanessa's dress proved to even more jarring when she stood alongside her then-boyfriend, Donald Trump Jr., in his very vanilla black-and-white tuxedo. While Operation Smile is a very wonderful organization with an incredible cause, Vanessa's get-up practically begged the powers that be to make their next mission "Operation get Vanessa a stylist."

Donald Trump Jr. caught some serious flack when it was revealed that he scored Vanessa Trump's four-carat $100,000 engagement ring for free in exchange for a photo op of him on bended knee in the New Jersey Short Hills Mall jewelry store he got it from. Even his famous father publicly admonished him for the decision. "You have a name that is hot as a pistol, you have to be very careful with things like this," Donald J. Trump said during an appearance on "Larry King Live" (via the The New York Times). Alas, Vanessa didn't come out of the scandal unscathed either.

As reported by the New York Post, Don Jr. had already popped the question to a surprised Vanessa at their West Side apartment. Cue the waterworks. Sadly, Vanessa wasn't exactly dressed to impress when she arrived for proposal 2.0 at Bailey, Banks & Biddle jewelry store. Instead of going for a more timeless, classic bridal look, Vanessa showed up to the reenactment wearing a black blazer, a colorful statement necklace, a metallic belt, and a pair of skinny khakis. A blazer? Really? Very 2004.

It's widely been reported that Donald Trump Jr. was a bit of a cheapskate during his marriage to Vanessa Trump. "He gives her very little help and has been keeping her on a tight budget. She doesn't live a lavish life and can very rarely pick up a check at dinner," one insider told Page Six in 2018, shortly after the news broke that Vanessa had filed for divorce. Another claimed, "Don Jr. was never generous with money. Vanessa has had to rely on her mother for financial help for her personal needs."

Perhaps that's why Vanessa's Playboy bunny costume for the Roberto Cavalli Vodka and Giuseppe Cipriani Halloween Party in 2007 fell so flat. As evidenced in photos, Vanessa opted for an ill-fitting, all-black slip dress and a pair of knee-high boots that cut her figure right in half. Not exactly flattering. If only Don Jr. had given Vanessa the green light to enlist a professional stylist to help pull the look together. Sigh.

Vanessa Trump turned heads when she turned up at the third day of the 2024 RNC sporting an uber-casual white T-shirt and white jeans. (Alexa, play "White Tee" by Dem Franchize Boyz.) Although the laid-back white tee 'fit appeared to be reserved for the goings-on before the actual convention started, she kept the all-white monochromatic vibes going the entire time. On night three, she opted for a white-on-white sleeveless shirt and skirt set while sitting in the VIP section and watching her eldest daughter, Ivanka Trump look-alike Kai Trump, deliver a glowing speech in honor of her grandfather. The following evening, Vanessa appeared in the VIP box once again, this time sporting a seriously casual look given the caliber of the event: an all-white blouse and what appeared to be a pair of denim jeans. 

Fortunately for Vanessa, the public seemed to be more interested in her interaction with her ex-husband than her outfit. Don Jr. and Vanessa's 2024 RNC behavior confirmed what we suspected about them post-divorce, namely that they are great co-parents. Kudos to them!

We would be remiss not to discuss the crossbody bag of it all. Vanessa Trump made a serious fashion statement when she showed up at Donald J. Trump's second Inauguration in 2025 sporting an ill-matching, stark white, studded crossbody bag splayed across her otherwise polished navy coat dress. The decision proved to be such a fashion misstep that it landed her on the inauguration's best- and worst-dressed guests list (in Vanessa's case, the worst) curated by the Daily Mail. One would think that for an event of this caliber, a tasteful clutch would have been the more appropriate choice for the former model.

Sadly, that wasn't the first the public had seen of Vanessa's affinity for the crossbody. As evidenced in photos Kai Trump posted on her Instagram (including the one above), her mom opted to wear yet another crossbody bag to the pre-Inauguration fireworks display President Trump hosted at Trump National Golf Course in Sterling, Virginia. And just in case you're wondering, yes, this crossbody was also decked out in studs. While we understand that a crossbody bag might be the epitome of practicality when raising five children, one might argue that Vanessa would have been better off going the form-over-function route this time.