All eyes have been onDonald Trump Jr. since he reportedly ditched fiancee Kimberly Guilfoyle for his alleged mistressBettina Anderson.
Before there was Guilfoyle, though, there was his ex-wife Vanessa Trump.
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 ofVanessa, she has had quite the transformationover the years.
The model wore a steel blue satin-y dress with simple hair and makeup and big statement earrings.
And, let’s just say some pasties or a backless bra would have made all the difference here.

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.
The dress' cut didn’t leave much to the imagination.

Thanks to the garish print, this dress really never should have made it out the door.
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.
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.
