Vanessa Trump's Inappropriate Charity Gala Outfit Will Always Haunt Her

Vanessa Trump shocked partygoers with her outfit choice when she attended the Operation Smile Gala in 2008. She arrived wearing a gray satin mini dress that featured sequin embellishments along the bust. Vanessa's curious gala choice, which looked more like a glamorous nightie than something one would leave the house in, was inappropriate given the event. The night was a fundraiser for children, and Vanessa's dress was far too intimate and lingerie-like for the innocent, philanthropic atmosphere.

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Vanessa attended the New York City event with her then-husband, Donald Trump Jr. The two frequented the Operation Smile fundraiser throughout their years in New York, so the charity that helps children with facial deformities was clearly important to them. The couple met in 2003 at a fashion show in New York after they were introduced by Donald Trump. They married in 2005 at Trump's Mar-A-Lago resort in Florida and went on to welcome five children. At the 2008 gala, where Vanessa wore her risqué gray dress, she and Don Jr. were already parents to their oldest child Kai, who was born in May 2007 was then 1-year-old.

While Vanessa Trump made a poor choice in attire at the 2008 Operation Smile Gala, she redeemed herself in 2010. Attending the same event two years later, Vanessa arrived in a floor-length blue gown that felt much more suitable for the occasion. We want to give her the benefit of the doubt — she may have been aiming for a glamorous look at both galas, even with the wildly inappropriate lingerie-like dress. Fortunately, in 2010, she nailed the black tie dress code with her gradient halter dress and sparkling necklace, sporting a tonal clutch with her hair styled sleekly in a middle part.

Vanessa's style has been hit or miss over the years. While Vanessa looks stunning makeup-free, she's made some strange fashion choices at various events. Vanessa once wore an inappropriate outfit to a wedding, making one of the biggest faux pas' imaginable. (Hint: guests can't wear white!) She's one of the many Trump women whose outfits have totally missed the mark, though that gray slip dress might go down in history as one of her worst looks.