Vanessa Trump's Most Inappropriate Outfits Yet

All eyes have been on Donald Trump Jr. since he reportedly ditched fiancée Kimberly Guilfoyle for his alleged mistress, Bettina Anderson. But before there was Guilfoyle, there was his ex-wife, Vanessa Trump. Besides Don Jr. himself, all these women have something specific in common: they walk a fine line between celebrity socialite and political figure in which their outfit choices, favorite designers, and even the way they accessorize are scrutinized and judged by millions of people.

By now, we all know that Kimberly Guilfoyle has sported more inappropriate outfits than the rest of Don Jr.'s past partners combined, but that doesn't mean his ex-wife, Vanessa, has a flawless fashion record either. Vanessa, a former model, has made some questionable sartorial choices that lead us to believe she's no expert in fashion. Her financial abundance also isn't enough to make her outfits stand out for all the good reasons — does she even have her own stylist? It's giving, not.

Even though Vanessa Trump has had quite the transformation, she's committed some serious fashion faux pas. From basically wearing lingerie to a charity event to one of the worst Playboy bunny costumes we've seen, Vanessa has proven that even those with modeling experience aren't immune to wardrobe blunders.

Black-tie events have special rules, and while Vanessa Trump's satin, figure-hugging gown at the Operation Smile "Smile Collection" Couture Event in 2004 probably fit the rules, it still stuck out like a sore thumb. 

The dress' plunging cut didn't leave much to the imagination, which veered into inappropriate territory. While this frock feels a bit risky for a formal, black-tie charity event, there are really no rules against it. When the dress has an extremely bold and glaringly ugly print, however, it drew even more attention to the look. Something subdued would have worked much better for this occasion.

Vanessa's hair and makeup at the party looked perfect, but a simpler gown would have been a much more fitting choice for the occasion that complemented her glam. Next to Donald Trump Jr. in a classic tux, the couple looked mismatched, as if they were attending two entirely different events. Thanks to the garish print, this dress really never should have made it out the Trump residence's door.

In 2005, Vanessa Trump attended the launch of Rock Candy in New York City alongside her then-fiancé Donald Trump Jr. The model wore a steel blue satin dress with simple hair and makeup and long, dangly statement earrings. The ensemble was proof of just how aggressively the wrong fabric can take an otherwise good look and make it just plain bad. The dress, itself was fine, but the fabric showed everything — including wrinkles and all that was going on underneath. And, let's just say — some pasties or a backless bra would have made all the difference here. 

There's certainly nothing wrong with going braless — even in a dress that might have fabric that's a bit on the thinner side. The problem here is that the dress' sheen and lack of lining made what was going on underneath so obvious that it was almost like another accessory. For an event with a red carpet, this just felt like a bit much, especially since other guests were in evening wear. 

In 2006, Vanessa Trump was invited to an event that any pet-lover would adore. She was asked to walk at the yearly fashion show thrown by Animal Fair Magazine. Seeing that the theme was "Paws for Style," Vanessa could have worn any number of cute, pet-friendly outfits. In the past, other celebrities — like Angela Kinsey and Paula Abdul — had already attended the event in jeans and comfy tops — in other words, the type of casual wear that one might wear to take their furry friend on a walk. Vanessa should have probably chosen to follow suit. Instead, she appeared at the event in a shocking combination of colors that brought to mind one of the most anti-dog super villain's in cinematographic history: Cruella de Vil from Disney's "101 Dalmatians."

Yes, Donald Trump's former daughter-in-law showed up at the fashion show wearing a lacy white blouse and a long black coat. While there would usually be nothing wrong with this color combination, the fact of the matter is that black and white are known as Cruella's signature shades. In addition to supporting black and white hair throughout the "101 Dalmatians" movie, the super villain wears different combinations of these colors. Her most famous outfit is probably her iconic slinky black dress, which she pairs with a white mink coat. The fact that Vanessa wore the converse of this outfit to a pet-centered event was not just odd but also inappropriate.

In 2007, Vanessa Trump attended the Roberto Cavalli Halloween party dressed as a Playboy bunny — a choice that raised eyebrows no just for its boldness, but because the event was in aid of Children in Crisis and The Happy Hearts Fund, both charities dedicated to supporting vulnerable children. 

While the Playboy bunny look is a recognizable Halloween staple and costume classic in the early aughts, wearing it to a fundraiser for child-focused organizations sent a jarring message. The revealing, lingerie-inspired outfit clashed with the nature of the cause, undermining the tone of the evening meant to spotlight compassion and care for young people in need.

Furthermore, the costume was an example of poor styling, too. The dress Vanessa wore was a bit too long for sheer tights and over-the-knee boots. These accessories would have looked better with a much shorter hemline. Mostly, the outfit looked like the Trump wife just tossed some Spirit Halloween accessories on with a night dress and called it a day. In the context of the event, the costume wasn't simply a mismatched mess and a risqué party choice — it was a tone-deaf misstep at an event where the beneficiaries were children's charities.

Is there ever a good time to throw on your shiny silver bedazzled lingerie with some flat beach-ready strappy sandals and hit the town? Probably not. But, if there is ever an occasion for this, an event for a children's healthcare nonprofit organization is definitely not it. Apparently, though, this isn't something Vanessa Trump cared to think about when choosing an outfit for the charity event. 

In 2008, the Trump wife attended Operation Smile's fifth annual Smile Gala in a metallic, mini-slip dress. This would have been a better look for an organization called Operation Cringe, or a party at the Playboy mansion, or ... bed!

Vanessa's dress looked more like wedding night lingerie than evening wear, and the event's other attendees were, in fact, wearing evening wear. The bedazzling details at the top of the frock somehow managed to make it look even more like sleepwear, and her styling didn't do anything to dress up the garment. The slip dress was just way too casual for such a special occasion, and for such a good cause. In our opinion, it would have looked much better if she had saved this one for a night at the club.

When Donald Trump first announced his intention to run for president in 2015, he gathered alongside his family at Trump Tower in New York. Since then, a lot has changed. The Trump family's faces have transformed considerably with age since that iconic day, and the list of family members has also shifted. Vanessa Trump famously ditched the dynasty in March 2018 after filing for divorce from Donald Trump Jr. Interestingly, she made this move just a couple of years after posing in front of the Trump podium with the rest of her husband's family. Perhaps she never fully fit in with the Trump crew.

A closer look at the photographs from the presidential campaign announcement reveal that Vanessa stood out from the rest of the Trump women. While Ivanka Trump, Melania Trump, Lara Trump, and Tiffany Trump all wore skirts or dresses, Vanessa seemed to shirk the dress code. Instead, she showed up to the event in an ink-black power suit, which she accessorized with black pumps. This move seemed almost defiant, as the only other people in the entire group to don similar attire were the boys and men. Although it's hard to say why Vanessa made the fashion choice that she did, it goes without saying that she stood out from the rest of the crowd. This made her outfit — as amazing as it was — inappropriate for the occasion.

While Vanessa Trump's outfit at Donald Trump's 2017 inauguration may have looked good, it was her pair of white tasseled earrings that caused a stir. Although the jewelry matched nicely with her burgundy coat, there was one major problem: Vanessa's earrings appeared to have originated from Ivanka Trump's jewelry brand.

Vanessa's choice to wear one of Ivanka's products — that reportedly cost $12,500 a pair — to a political event created an overall feeling of discomfort for some spectators. After all, it seemed that Vanessa might have been trying to use the Trump family's political fame to promote her sister-in-law's business interests. Speaking to Yahoo News! about this ethical gray area, Julie Zerbo of The Fashion Law blog explained, "Conflict of interest laws do not bar a president or his family from involving themselves in endeavors that could boost their private companies's profitability or level of exposure. Does it stand to look bad? Yes. But is it illegal? No." While Vanessa's outfit did not break any laws, it was widely considered to be inappropriate. 

Things between Vanessa Trump and Donald Trump Jr. may not have been meant to last, but that doesn't mean there wasn't another special somebody waiting for the mother of two. On March 23, 2025, golfing sensation, Tiger Woods, took to Instagram to announce his budding romance with Vanessa. While some spectators have guessed that Tiger Woods and Vanessa Trump's relationship won't last, the couple seem pretty optimistic about their chances. As Woods himself captioned his post, "Love is in the air and life is better with you by my side! We look forward to our journey through life together."

Less adorable, though, was the outfit that Vanessa wore in the photo announcing their relationship. Dressed in a pair of jeans and a white tank top, the former model should have looked casual yet confident. Instead, though, she appeared awkward for one simple reason — her tank was transparent enough that her underclothes were extremely visible from beneath. While this is a common issue for people wearing bras beneath white shirts, there is an easy way to prevent this. Vanessa could have simply wore a nude colored under-shirt or bra beneath her top, allowing the piece to blend in with the natural tone of her skin. Unfortunately, this fashion fail proved to be extremely inappropriate, as it detracted attention from Vanessa's new relationship and redirected it toward her poorly-planned outfit. 

There are inappropriate outfits, and then there are straight-up faux pas. In spring 2025, Vanessa Trump was called out for committing one of the greatest fashion offenses of all times — wearing white to someone else's wedding. As per a photograph shared to her daughter Kai Trump's Instagram, Vanessa attended some nuptials in a silvery white dress with a pleated skirt. Although she paired the outfit with a soft camel cardigan and a pair of sparkly gray heels, Vanessa did nothing to disguise the color of her frock. Instead, her accessories just accentuated the controversial color scheme by creating a bit of contrast. To add insult to injury, Vanessa even painted her toenails white, highlighting the unusual shades of her attire.

While the old tradition of not wearing white to a wedding may seem out of date, there's a reason behind this common piece of etiquette. Guests are not meant to steal attention from the people who are actually getting married. Even sporting off-white shades is unacceptable. "As long as the main color doesn't read as white, you're in the clear," bridal stylist, Anny Choi, told Vogue. With this in mind, guests should avoid white and all white-adjacent shades like the plague — even if they have a famous name like Vanessa Trump.

If wearing white can be a controversial decision, wearing black can be even more polemic. The reason? Black is traditionally a color associated with funerals and mourning. As a result, wearing this shade to a celebratory event can be wildly inappropriate. Despite this, Vanessa Trump decided to wear black to her daughter, Kai Trump's, 18th birthday bash in May 2025. On this occasion, Vanessa took the young Trump on a girls-only shopping spree in New York City. The massive buying bash was followed by dinner at the pricey sushi restaurant, Nobu. (Yes, we know, Kai Trump lives a lavish life). But, because Kai's birthday was meant to be celebratory, it would have been expected that Vanessa wear vivid spring colors. Unfortunately, however, she went with something totally dour.

Video footage of the event — which was later shared on Kai's YouTube channel — shows Vanessa doing a fake catwalk down the streets of Manhattan. Although Vanessa clearly meant for this moment to be cute, her all-black outfit couldn't help but draw attention away from the joy of the moment. She essentially wore the shade from head-to-toe, sporting a black sweater, black straight-leg slacks, and a pair of dramatic black heels. The only contrast in her look was a dark gray shirt, which she layered beneath her sweater, and a brown clutch bag. The result was a drab look that was simply inappropriate for a birthday party.

Kai Trump's birthday party was not the only time that video footage from the Gen Z's YouTube channel would shed light on one of her mother's fashion faux pas. In August 2025, Kai released a new vlog post titled "My mom took me to the HAMPTONS!" The video, which highlighted life at one of New York's most exclusive beach getaways, also revealed something disappointing about Vanessa Trump's wardrobe choices — the socialite does not exactly dress up on airplanes. As shown in the final portion of Kai's YouTube video, Vanessa decided against dressing nicely on her flight home from The Hamptons. Instead, she sported an army green fleece and a pair of blue jeans. 

While this outfit would certainly be appropriate for a day on the couch, experts warn that it isn't ideal for air travel. As etiquette coach, Jodi RR Smith, explained in an interview with USA Today, dressing nicely on an airplane is a way to express politeness. "In my perfect world, passengers would wear lovely, lightweight, loose-fitting, long-sleeved and long pants outfits," Smith said. Speaking to USA Today for the same article, frequent flier Neil Chase seemingly concurred: "It isn't about stifling individuality, but fostering respect and comfort for all." With this in mind, it is rather unfortunate that Vanessa Trump has failed to don sufficiently appropriate attire when flying — despite her undeniable wealth and penchant for expensive clothes.