Vanessa Trump's Most Inappropriate Outfits

While Vanessa Trump has been making headlines for the potential red flags in her relationship with Tiger Woods in 2025, there was once a time in the '90s when she was just an up-and-coming model on New York's Upper East Side. Her notoriety rose quickly, as she was suspected of having developed romances with Leonardo DiCaprio, Latin Kings gangster Valentin Rivera, and Prince Khalid bin Bandar bin Sultan Al Saud. By 2003, she would meet her future ex-husband Donald Trump Jr. and open her nightclub, Sessa. As her reputation steadily increased, she began attending red carpets, openings, galas, and all the works, and as a 20-something at the time, many of her ensembles either leaned on the risqué side of things or were completely understated. We can't blame her; it's the same duality you face in college as you change out of the athleisure you wore to class into the shreds of fabric you wore to go out on the town.

Don't get us wrong: Vanessa Trump has had a stunning style transformation. Eventually, Vanessa and Donald Trump Jr. tied the knot in November 2005, later welcoming Kai Maddison Trump in May 2007, Donald John Trump III in February 2009, Tristan Milos Trump in October 2011, Spencer Frederick Trump in October 2012, and Chloe Sophia Trump in June 2014. As you can probably imagine, this meant Vanessa had other things on her mind besides putting outfits together and making sure they were appropriate. We don't blame her, since everybody gets it wrong sometimes, but a few of her looks over the years simply didn't fit for one reason or another, and these provide a good lesson for the fashion-conscious in how to avoid inappropriate dressing. 

Vanessa Trump attended the Anniversary Celebration of Gotham and LA Confidential Magazines in February 2004, and really felt the need to bundle up, likely because her base layer was see-through. She stepped out onto the red carpet in pointed-toe black leather boots and wore a long-sleeved bodycon dress. The dress layering over the skirts weirdly skews the proportions, but the excessive fabric wasn't enough to keep Vanessa covered up. Around her chest area, the material looks so thin that you can nearly see underneath. This is certainly a questionable look, but it explains why she felt the need to carry both a jacket and a scarf.

Vanessa Trump spent Halloween 2007 at the Roberto Cavalli Vodka and Giuseppe Cipriani Halloween Party that benefited Children In Crisis and The Happy Hearts Fund, but her costume was more "adult entertainment." She chose to dress up in a costume that may as well be a rite of passage: a Playboy Bunny. For the look, she wore a black slip dress with fishnet tights and thigh-high boots, accessorizing with cuff links, a fuzzy collar, and bunny ears. It was a lazy attempt at an iconic costume, and it seemed as though she threw it together at the last minute. If you're going to do it, at least do it right.

Vanessa Trump rolled out of bed before hitting the red carpet for Operation Smile's annual Smile Gala in May 2008 (hopefully that means she brushed her teeth before running out the door). The former model wore a blue-silver satin slip dress with an embellished bustier and flat, strappy sandals. To make matters worse, the only accessories she wore were a few dainty rings and earrings. No bag, necklaces, or bracelets, and her nails and toes weren't manicured, as if she had no care in the world before calling it a night. Yikes.

If Vanessa Trump's wearing an inappropriate outfit, it's likely because it's see-through. In September 2007, Vanessa attended the BCBG Max Azria collection show during Mercedes-Benz Fashion Week, and stuck out like a sore underdressed thumb compared to the designer fashions of those around her. Instead, she opted for a sheer white blouse with a white bra underneath. It would be one thing if the look was deliberately scandalous, but the babydoll top with delicate embroidery seems a bit too pure for this to not have been a fumble. 

Vanessa and Donald Trump Jr. made the October 2012 premiere of "Secret of the Wings" a family affair, but if only they had discussed their outfits before heading out the door. Vanessa was pregnant at the time, but her maternity outfit was slightly villainous. She opted for a black maxi dress with a gray cardigan and a chunky beaded necklace. We'll excuse her uninspired ensemble since she was pregnant; however, juxtaposed against the brightly costumed characters and her husband's vibrant shirt, basing her look around black doesn't exactly scream, "The Happiest Place on Earth!"

No wonder we haven't seen Vanessa Trump at a fashion show for so many years; it's starting to seem as though she's never followed the dress code. For the Carolina Herrera fashion show in March 2014, Vanessa was once again heavily pregnant. She decided on a gray-blue long-sleeve top with a baby-blue short-sleeve sweater over it, and white jeans. Layering may have been a fad for a second in the 2010s, but that doesn't mean it was a good one. Even if it were, standing next to her husband in a shirt and a blazer made her seem completely underdressed for the event.

Vanessa Trump celebrated her oldest daughter's commitment to the University of Miami the only way she knows how: with a see-through ensemble. In a carousel of photos, Kai Trump, who has had quite the transformation of her own, posted to Instagram, one of the pics showed both of them, throwing up the "U." Their outfits were coordinated, which is a first; however, perhaps Vanessa's look was a bit too scandalous. She wore a cream ruffled skirt and a sheer blouse that left nothing to the imagination, which is less than appropriate for a snap with her daughter to celebrate college. At least her bra matched the rest of the outfit.