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Vanessa Trump’s slip dress phase was full of inappropriate timing, and it wouldn’t have been complete without a Halloween costume in the mix. Back in October 2007, Vanessa attended Roberto Cavalli’s Halloween party with then-husband Donald Trump Jr. Five months postpartum with their oldest daughter, Kai Trump, Vanessa went as a lingerie-clad Playboy Bunny. For the event, she paired a black, satin nightie with lace detailing with dark stockings and thigh-high boots (with no heel, we might add). She accessorized her look with the signature bunny ears, fuzzy choker, and wrist cuffs that can easily be found at your local Spirit Halloween.
It’s difficult to decide where to begin our grievances with this look, and we’ll ignore the fact that it seems like she threw it together in five minutes. We understand that Vanessa was trying to maintain some modesty by wearing the slip dress, but all it did was skew her proportions. Her legs looked incredibly short, which wasn’t helped by the tall suede boots and lack of heels, and her costume looked incredibly cheap, especially compared to other guests at the party, who wore expensive-looking gowns and feathered outfits. Additionally, Don Jr. arrived dressed as a cowboy, which didn’t match her look whatsoever. Couples aren’t obligated to wear coordinating costumes, but this duo looked more cohesive post-divorce than they did at this party.
Vanessa Trump has had other polarizing Halloween costumes
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For Halloween 2024, the gang got back together, including Donald Trump Jr., Vanessa Trump, and Kai Trump. Before we unpack the group costume, though, we’ll explain why this trio being together was so odd. Vanessa and Don Jr. got married in 2005, and after welcoming five children, the two publicly declared their divorce in March 2018. There didn’t seem to be too much animosity at the time, as Vanessa filed for an uncontested proceeding and they likely had a prenup, according to Page Six. However, it didn’t take long for Don Jr. to find love again in Kimberly Guilfoyle. The two began dating in the spring of 2018, and he got on one knee on New Year’s Eve in 2020. (It wasn’t until February 2025 that sparks flew for Vanessa Trump, who entered a relationship with Tiger Woods despite the red flags flying around them.)
Now, let’s analyze their costumes. Kai posted a carousel to Instagram, and in the photos, she and her mom are wearing white garbage-man jumpsuits, while Don Jr. is wearing a poncho with trash duct-taped to it and a red “Make America Great Again” baseball cap. We’d be lying if we said we weren’t confused as to what they were going for. Sanitation department realness, perhaps? Another user posted the photo and took their guess, writing in the caption, “Donald Trump Jr with the BEST HALLOWEEN OUTFIT! WE ARE ALL GARBAGE according to Biden/Harris! TRUMP-VANCE 2024!” The most bizarre aspect of the family outing, though, was that Guilfoyle was nowhere to be found.
Many of Kimberly Guilfoyle’s Halloween costumes are similar to Vanessa Trump’s Playboy Bunny
In many cases, Kimberly Guilfoyle’s Halloween costumes have tended to show a lot of cleavage — not dissimilarly from Vanessa Trump’s 2007 look. They’ve also looked a little cheap at times, but hey, what can you do?
In October 2019, Don Jr. and Guilfoyle did something as a couple that he and Vanessa wouldn’t do for a few more years: wear coordinating couple’s costumes. To promote Don Jr.’s book, “Triggered: How the Left Thrives on Hate and Wants to Silence Us,” Guilfoyle wore a figure-hugging black dress with purple embellishments and a witch’s hat, while Don Jr. was in head-to-toe camo and carrying a bow and arrow. Together, they were an actual “#witchhunt,” as Guilfoyle put it in an Instagram post from the time.
Kimberly Guilfoyle has dressed as both Snow White and her wicked stepmother: pic.twitter.com/zSZBUYtUQN
— Paul Rudnick (@PaulRudnickNY) November 19, 2023
A few years later, for Halloween 2023, Guilfoyle attended a celebration at Mar-A-Lago as the original Disney princess, Snow White. Obviously, it doesn’t hold a candle to Kimberly Guilfoyle’s most inappropriate outfits, but it seems as though she was accidentally shopping in the kids’ section, as the tiny, wrinkled dress didn’t leave much to the imagination. Of course, the look wouldn’t be complete without a tiny plastic crown.
