Vanessa Trump's Slip Dress Phase Was Full Of Inappropriate Timing

Whether they were born into the Trump family or married into it, the women in Donald Trump's inner circle have become notorious for their highly questionable, and often inappropriate, ensembles. Beyond that, many of them have gone through phases of specific garments or methods of styling, like when Ivanka Trump kept wearing outfits with hidden meanings. Donald Trump Jr.'s ex-wife Vanessa Trump is no different, and her poison was the slip dress.

Not that a slip dress isn't always an option; after all, the garment can be transitioned into fall or any other season. The satin material and thin straps allow it to be breathable, yet still chic. However, as it is originally intended to go under clothing or be worn as sleepwear, there are certain ways that the slip dress should be elevated, and despite using some of these, Vanessa still fell flat with her styling. What resulted was a string of red-carpet looks, mostly from the mid-2000s, that were both too lackluster and largely inappropriate for the occasion. Let's take a look back at some of Vanessa Trump's worst slip-dress offenses.

One of the first times Vanessa Trump stepped out in a slip dress was for the 2nd Annual Partnership for Public Service Gala in June 2004, and it wasn't even her worst infraction. The violet dress was floor-length and featured a double-strap detail on both arms. Vanessa paired the garment with dangly statement earrings and a dainty necklace. However, with the plunging neckline and form-accentuating material, it still seemed a bit risqué for an event honoring public service, not to mention the fact that the skirt wasn't steamed before the upscale function.

Someone call the fashion police! Doesn't Vanessa Trump know that even if you're attending two events on the same day, you have to change your outfit or you're deemed an outfit repeater? Apparently this was news to her, as she wore the same baby-blue slip dress to both the launch of Rock Candy and the opening night reception of Veranda: New York's Best at Trump Park Avenue, but we can't tell which one she's more out of dress code for, especially since the material left nothing to the imagination.

You're allowed to wear whatever you want on your birthday, but you'd think that for a milestone like turning 30, Vanessa Trump would choose something slightly more versatile than yet another slip dress. For her special day in December 2007, she decided on a metallic silver slip dress, pairing it with a chunky layered necklace and red dangly earrings. While the color and accessories certainly gave 30, flirty, and thriving, the cut and shape of the dress just gave frumpy. Vanessa could've simply added a belt or a stylish leather jacket to elevate the look entirely.

It's a rite of passage in a woman's life to go as a Playboy bunny for at least one Halloween, and Vanessa Trump's time came in October 2007, right in the thick of her slip-dress phase. For Roberto Cavalli's Halloween Party, she opted for a black slip dress with lace detailing, dark stockings, thigh-high boots, and the bunny accessories you can expect to find at any store that sells costumes: bunny ears, a fuzzy choker, and wrist cuffs. Such little effort went into this look that the end result was too lackluster for Halloween.

Vanessa Trump attended Operation Smile's 5th Annual Smile Gala in May 2008, and though her dress sparkled like a bright smile, it still wasn't quite refined enough for the red carpet. Vanessa ventured away from her usual slip-dress silhouette by wearing one with an embellished bust. However, instead of adding class to the ensemble, it merely made it look like she was wearing a sequinned bra with a silver skirt. She went from her previous sexy nighttime looks to an even more sultry nighttime look that resembled lingerie, not a gala outfit.

"It's not a phase, mom!" Vanessa Trump yells after we tell her to donate all her slip dresses from the 2000s, and she proved that when she attended the Breast Cancer Research Foundation's Pink Carpet Party in April 2015. Donald Trump Jr.'s ex-wife did upgrade slightly by donning a floor-length slip dress for the first time in years, but it wasn't enough to save the look. The sand-colored garment featured stitch detailing on the bust and midsection and loose pieces of fabric, making it appear torn. This together with the creased skirt ultimately made for an outfit that appeared too distressed and sloppy for a black-tie function.