Vanessa Trump Outfits That Just Didn't Work

The Trump family has worn some tragic outfits over the years. That said, Ivanka Trump rarely puts a stylish foot wrong, and Melania Trump's ludicrously expensive outfits usually guarantee she looks classically stylish. Unfortunately, the same can't be said for some of the inappropriate outfits Lara Trump has been caught wearing — and, let's face it, the less said about Kimberly Guilfoyle's clothing choices, the better. However, her predecessor, Vanessa Trump, was a pro at balancing style and practicality. Still, even she was known to commit a fashion crime occasionally.

Vanessa was well-versed in the style world before entering the Trump sphere. She was a Manhattan socialite who was signed to the prestigious Wilhelmina Agency and frequented all the hottest clubs. Vanessa's rumored to have hooked up with Hollywood's infamous unofficial model scout, Leonardo DiCaprio. Oh, and she launched her own handbag line, La Poshett.

However, it all changed after Vanessa met Donald Trump Jr. at a fashion show in 2003. In November 2004, he showed his romantic yet thrifty side by proposing with a ring he scored for free in return for promoting a jewelry store inside a New Jersey mall. Five kids followed, as did rumors of infidelity. In March 2018, the couple decided their marriage didn't work anymore, and Vanessa filed for divorce. During their years together, a bunch of Vanessa's ensembles didn't work either. But sadly, she couldn't erase them as easily as she did her ex-husband. We're taking a look at five of her unfortunate outfits.

Vanessa's high-heeled bowling blunder

Some people in the USA take their bowling very seriously. There are thousands of different leagues to compete in across the country, many specially designed shoes to fit every need, custom-designed shirts, carefully molded balls, and hand-crafted bags to carry precious sporting cargo. Vanessa Trump, though? Nah, she doesn't take bowling too seriously at all.

In fact, Vanessa's bowling outfit just didn't work — in the slightest — when she played a January 2017 game at the White House, which presumably has a bowling alley inside its hallowed halls. Who knew? Donald Trump Jr. posted a video of his wife's impressive arm swing as she delivered the ball, clad in a skirt, belted coat, and high heels. Considering Vanessa's inappropriate outfit, she didn't do too badly at all, scoring a fast eight on her first go. Even Don Jr. was forced to grudgingly praise Vanessa's delivery deftness. "Family bowling session at The White House. @MrsVanessaTrump is doing pretty well, considering she's in heels," he posted on X, formerly known as Twitter.

Not surprisingly, the responses to the video were mixed. However, a disproportionate number were from concerned citizens worried about the bowling alley's flooring. "That's a fun, appropriate video. But really, she should take off her heels so as not to damage public property," one commented. "Enjoy the bowling. But bowling shoes will improve your game and protect the wood flooring," another explained.

Vanessa's unceremonious engagement attire

Apparently, or at least according to many an outdated kids' book and flick, every young girl dreams of getting married to her prince (or princess) one day. It's a highly debatable fairytale narrative, but one thing that can't be disputed is the number of people who love watching shows about engagements and weddings. According to Forbes, 3 million viewers tuned in to watch a spin-off special of TLC's "90 Day Fiancé" in August 2022, making it the most-watched non-news cable TV show. Meanwhile, Gitnux estimates over 2 million people watched the Season 9 premiere of "Married at First Sight."

So, it's clear that people like watching others get engaged and/or hitched, which was both a blessing and a curse for Vanessa Trump. Sadly, given the circumstances — her spendthrift fiancé struck a deal for a free ring in return for promoting a jewelry store in a New Jersey mall — Vanessa unwittingly found herself in an outfit that didn't work for what was supposed to be one of the happiest days of her life.

In fact, poor Vanessa was clad in a simple blazer and jeans, without the opportunity to even get a quick manicure before the close-up shots of her ring finger began. Meanwhile, Donald Trump Jr. looked particularly happy with himself, dressed in a pinstripe suit, blue checked shirt, and tie, holding on to Vanessa tightly and ensuring her finger was angled at the best photo op position. And they say romance is dead.

Oy Vey! Vanessa's bat mitzva mini dress disaster

Vanessa Trump's bat mitzvah outfit definitely didn't work. Vanessa wore a fabulously flattering thigh-skimming navy-colored mini dress and high heels, which would have looked amazing for enjoying cocktails with some pals at Tigre. However, it didn't fit in quite so well to celebrate Arabella Kushner's coming of age in June 2023.

To make things worse, Donald Trump Jr. also attended with Kimberly Guilfoyle. However, it was Vanessa's tanned and toned legs that were the center of attention, not her ex's new fiancée, who was dressed uncharacteristically appropriately for once.

These days, it can be confusing what to wear for a bar or bat mitzvah, especially when it's held by Orthodox Jews — which Jared's family is — but, according to L'Chaim San Diego magazine: "At Orthodox parties, kids and adults should be respectful of the traditional dress code even if [they] are not observant. This means, as a minimum, skirts that cover the knees and elbow-length sleeves." Poor Vanessa.

Vanessa's Operation Smile sexy slip slip-up

Vanessa Trump brought some serious heat to the red carpet in May 2008. She was attending Operation Smile's 5th Annual "Smile" Gala at Skylight Studios in New York City. There was no doubt that she looked smokin' hot, dressed in a slinky silver mini night-slip with bejeweled top cups. However, all things considered, Vanessa's super sexy outfit didn't work well for a charity event.

In her pre-Donald Trump Jr. days, Vanessa was a successful model. She was signed to the prestigious Wilhelmina Models agency and rubbed shoulders with former Victoria's Secret Angel Karolina Kurkova. So, Kurkova may have hooked her pal up with one of her old Victoria's Secret ensembles for the night. Or, more likely, Vanessa enjoyed the fact that she could show off her bodacious body as she wasn't pregnant for once with one of the five kids she had during her 12-year marriage to Don Jr.

Just one year previously, Vanessa, looking radiant in a sparkling black fitted dress, narrowly missed giving birth to their daughter Kai Madison on the red carpet. "Her water broke while we were at a gala for Operation Smile's 25th Anniversary, and she was rushed to the hospital! She was a trooper at the event, but you could tell she wasn't feeling well," a friend told People in May 2007. Vanessa was also pregnant on the red carpet with Donald III in 2009, Tristan in 2011, Spencer in 2012, and Chloe in 2014.

Vanessa's bad bunny get-up

In fairness to Vanessa Trump, her 2007 Halloween bunny girl get-up might have actually worked if it wasn't for Donald Trump Jr. at her side. Because, as is often the case these days, Don Jr. messed everything up. This time, though, he did it by dressing as a bizarre mix of "Crocodile Dundee," a Montana hunter, and the late, great Toby Keith.

As hard as she had tried, though, Vanessa's outfit just didn't work. It wasn't helped by the fact that it looked like a last-minute dollar store get-up or something picked out from one of her five kids' dress-up boxes, with ludicrously long furry ears and a neck choker that looked like a mere afterthought. Don Jr. looked suitably smug, though, so all was not lost.

Don Jr.'s smugness could have been down to the fact he had finally gotten the chance to semi-cosy up to a semi-Playboy Bunny. He lamented in January 2007 that he missed his big opportunity to get down and dirty in the grotto back when a pregnant Vanessa accompanied him to the infamous mansion. "Can you believe the hell I'm going through? I'm at the Playboy Mansion with a pregnant wife!" he told Adam Carolla. "It doesn't get worse than that, does it? Now, I love my wife, but that is rough. And I'm going to pay for these statements later on tonight. I'm gonna pay."