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. Before there was Guilfoyle, though, there was his ex-wife Vanessa Trump. Because Don Jr. is in the public eye a bit more these days than he has been in the past, folks are interested not only in his new girlfriend but also in his exes. By now, we all know that Guilfoyle has likely sported more inappropriate outfits than the rest of Don Jr.'s past partners combined, but that doesn't mean that his ex-wife has a flawless fashion record.

Vanessa, a former model, married Donald Trump's oldest son in 2006. The pair had five children together during their twelve-year marriage before calling it quits in 2018. Like his relationship with Guilfoyle, Don Jr.'s infidelity reportedly led to his split with Vanessa. But during their time together, Vanessa sported some wildly inappropriate outfits to big events.

In defense of Vanessa, she has had quite the transformation over the years. And, while her hair and makeup routines may have gotten worse, her fashion has definitely improved over time. Even so, some of the outfits she had hanging in her closet in years past certainly qualify as skeletons in her closet. From basically wearing lingerie to charity events to one of the worst Playboy bunny costumes we've seen, we've got Vanessa's most inappropriate outfits over the years.

In 2005, Vanessa Trump attended the launch of Rock Candy in New York City alongside then-fiancé Donald Trump Jr. The model wore a steel blue satin-y dress with simple hair and makeup and big statement earrings. This 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. And, for an event with a red carpet — even a more casual one — this just felt like a bit much, especially since other guests were in evening wear. 

Wearing fur is, of course, a controversial fashion choice. It may not have been quite as controversial in 2006 as it is today, and if you were ever going to wear it, the Chie Imai Royal Chie Fur Collection reception would probably be the best occasion. Still, as far as we're concerned, these caveats do not excuse this truly horrible ensemble. The knee-length dress paired with the hip-length coat makes for confusing proportions. Pairing this with a T-strap sandal threw the proportions off even further by breaking up the line of her leg.

The silhouette of this ensemble was entirely weird, but ultimately, it's the ghastly combination of beige snakeskin and matching fur that really landed this look on the list. Ultimately, this outfit is giving less-fashionable Cruella de Vil vibes, and no matter what your style is, that's not the fashion statement anyone wants to make.

Black-tie events have special rules, and while Vanessa Trump's satin-y figure-hugging gown at the Operation Smile "Smile Collection" Couture Event in 2004 probably technically fit the rules, it still stuck out like a sore thumb. The dress' cut didn't leave much to the imagination. And, while this feels a bit risky for a black-tie charity event, there are really no rules against it. Pairing it with an extremely bold and glaringly ugly print, however, drew even more attention to the look when something subdued would have worked better. 

Vanessa's hair and makeup here looks perfect, but a simpler gown would have been a much more appropriate look for the occasion. Next to Donald Trump Jr. in a classic tux, the couple looked like they were going to two entirely different events. Thanks to the garish print, this dress really never should have made it out the door.

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 instinctively knew. In 2008, she attended Operation Smile's fifth annual Smile Gala in a metallic mini-slip dress. And, this would have been a better look for an organization called Operation Cringe.

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

Whether we like it or not, the Playboy bunny Halloween costume is a classic, and in the early aughts, it was in its prime. So, while we can't entirely blame Vanessa Trump for the choice to wear a Playboy bunny costume to the Roberto Cavalli Halloween Party in 2007, we can — and do — blame her for the execution. Once again, her styling gave her some weird proportions. The dress she 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, or she could have paired this dress with some pumps.

Despite the dress, itself, resembling lingerie, the styling made it stray so far from lingerie that it no longer fit the Playboy bunny vibe. Truthfully, the look she wore to the Operation Smile event actually looked more appropriate for a Playboy bunny cosplay. Mostly, it looks like she just tossed some Spirit Halloween accessories on with an outfit for going out to dinner and called it a day. And, that's bad enough for a high-end fashion designer Halloween party, but it's worth noting that she attended with Donald Trump Jr., who was wearing an equally bad cowboy costume, and these clashing looks made both costumes even worse.