Vanessa Trump Outfits That Completely Missed The Mark

Donald Trump Jr.'s ex-wife, Vanessa Trump, is a former fashion model — but it hasn't been enough to keep her from making some occasional appearances on the worst dressed list. She's been known to miss the mark at political events like the 2017 Presidential Inauguration. She's also embraced the '00s trends a little too intensely on the red carpet, seemingly adding boleros to the list of outdated trends Trump family women won't ever give up.

It's not clear whether she works with a stylist but, given her new, high-profile relationship with golf star Tiger Woods, she probably needs to find one — or fire whoever she's been working with. Either way, this beauty deserves a personal style upgrade that complements her natural loveliness rather than undercutting it. But Vanessa Trump has stepped out in a number of looks that are totally mismatched to the venue and occasion, proving that dressing well is a complex art form. And that model-worthy looks are no guarantee of success.

In 2006, Vanessa Trump and her then-husband Donald Trump Jr. attended an event at FAO Schwartz to fundraise for Operation Smile. She looked radiant in understated makeup — surprising, since overdone makeup is a signature makeup mistake in the Trump family — and tousled curls.

Below the neck, though, this look starts to fall apart. The first problem? There's just too much going on, from the layered necklaces to the uber-textured jacket. Her furry white bolero is oddly bulky and almost appears to restrict her movement. Plus, this layered piece was super trendy at the time, meaning the photo looks dated quickly. 

Meanwhile, Vanessa's shiny red gown hits just at the knee. She would have been better served by a flowing dress that ended beneath the knee, drawing the eye down and elongating her silhouette. Finally, the fit of the dress could be improved since it bunches at her waist, adding to the visual busyness of the ensemble.

When Vanessa Trump walked the red carpet for the Operation Smile Gala in 2008, she wore a short, silver dress that simply did not belong at a black tie event. While it's a pretty piece, it's cocktail length and too sexy for a formal event, especially one where the emphasis is on fundraising. Paired with the silver strappy sandals, Vanessa looks like she's headed out to dance at a club after hours — not support a global children's medical charity.

The satin texture is part of what gives this ensemble such an over-the-top sexy vibe, as well as the major cleavage on display. Combined with the dusting of sparkles, this is a dress that says "Look at me," which feels inappropriate for such a stately event where the emphasis is on helping others. Finally, while the slip dress made a comeback in the 2020s, this style just isn't super flattering for Vanessa Trump's silhouette, with the short dress leaving her looking top-heavy.

When Vanessa Trump stepped onto the runway at Animal Fair Magazine's annual "Paws for Style" fashion show, she was wearing light-wash bootcut denim, a girly white top, and a sparkly black duster. She completed the look with the silver strappy sandals she regularly wears on the red carpet, which seem to be a favorite. 

It's a cute ensemble, but it's strangely casual for what is billed as a fashion event. It just isn't as upscale as a charity fashion event warrants, especially with an embellished over-layer that looks like it could have come from '00s fast fashion retailer Forever 21. Even worse, the pants don't appear to fit her well. Wrinkling across the thighs suggests that they are a bit tight, and they don't quite skim the ground, meaning they're a bit short. In other words, this would be a great look for a casual Saturday spent running errands but it's just not appropriate for this venue.

Like Melania Trump, another former model who has been known to wear some seriously outdated fashion trends, it's obvious that Vanessa Trump has adapted her style to the arena of politics with mixed success. In this realm, ensembles are often treated as tacit statements, suits are standard, and artful dressing means finding relatively modest silhouettes. But Vanessa Trump has struggled to balance appropriate with flattering.

Nowhere was this more evident than at President Donald Trump's 2017 inauguration, when she wore a strangely cut coat. Given its January date, inauguration fashion tends to heavily favor stylish coats and coat dresses. And while Vanessa Trump managed this in theory, there's just a lot to be desired about this odd, plum-colored coat that cuts off abruptly mid-thigh. 

The placket is bulky and poorly balanced by the bottom half of the suit, which isn't long enough to cover her knee-length dress. The black dress hem hanging out of the bottom of her coat looks cheap and leaves her looking oddly top-heavy — not the sort of elegance that suits such a high-profile political event.

Vanessa Trump donned a strapless white gown for the 2016 White House Correspondents' Association Dinner. While there's nothing wrong with the dress itself, this look is a miss, since the true white color looks very severe against her platinum blond hair color and deep tan. There are plenty of colors that make blond hair pop, but this one stands out in all the wrong ways. 

For an event as formal at the annual Correspondents' Dinner, Vanessa Trump would be better suited with a gown that flatters her coloring and hides her super visible tan lines, which look tacky at a black tie event. This particular cut also emphasizes the breadth in her shoulders. 

While we're plenty jealous of that muscle tone, a halter or spaghetti strap neckline would offer a softening effect and help the overall look feel less harsh. Plus, a fuller skirt or detailing at the hips would draw the eye to the bottom half of her ensemble and accentuate her curves to balance out the width in her shoulders. While Vanessa Trump may have some fashion hits, this just isn't one of them.