Tiffany Trump's Most Inappropriate Outfits To Date

Tiffany Trump, the second-youngest of the Trump siblings and the only child of Donald Trump and Marla Maples, got married in Florida at Mar-a-Lago in November 2022, making headlines for her gorgeous wedding look. According to The Indian Express, Trump stunned in an Elie Saab sparkly, billowy gown with a fitted center, long sleeves, and a sweeping floor train. Her husband, Michael Boulos, is Lebanese, which inspired her to choose the Lebanese designer to make her simply stunning dress. "It's a Lebanese American wedding, so we were so happy to have Elie Saab create the magic," said the mother of the bride to People, who also wore an Elie Saab gown.

However, Tiffany Trump hasn't always made the right calls when it comes to fashion. Among some of her questionable choices, one look that comes to mind is when she sported a bright blue dress at the Republican National Convention. This may not seem like a fashion faux pas as Trump looked beautiful, but the color blue is associated with the Democratic party. Of course, many questioned Tiffany Trump's color statement that night — but it's not the only time the public has questioned her sartorial choices. Read on for Tiffany Trump's most inappropriate outfits to date.

She looked like a Bridgerton character when she traveled to the UK

Visiting the United Kingdom from the United States is always a treat, especially when Buckingham Palace is involved. According to The Guardian, in June 2019, the Trump family was invited by the late Queen Elizabeth herself to enjoy a holiday at the iconic and historical Buckingham Palace. 

The family's ensemble choices seem to garner some media attention, and not in the way of Vogue. Journalists compared Tiffany Trump's dress (and choice of accessories) to a character out of a Jane Austen novel.  As The Guardian wrote, "Tiffany appears to have typed 'Jane Austen World Book Day costume' into the Amazon search bar and came up with an evening gown in a shade of claret that gave her the vibe of a midwestern bridesmaid who is, like, really into 'Downton Abbey.'" Meanwhile, Tiffany's sister Ivanka took to her Instagram to post the family picture along with the caption, "A spectacular State Banquet hosted by Her Majesty The Queen at Buckingham Palace."

They are giving off more "Bridgerton" vibes if you ask us — we're now in the mood for some clotted cream, scones and tea!

She wore a Chinese designer as her father bashed China

Well, this is awkward. As Tiffany Trump's father, Donald, squawked on stage during a presidential debate in September 2016 — blaming China for stealing American jobs and devaluing American money, Tiffany sported a dress made by Chinese designer Wang Tao, who professionally goes by Taoray Wang (via Jing Daily).

The Beijing-born Wang is often called China's "Queen of the Suit" (via XinhuaNet) and, according to Jing Daily, is actually a descendant of a Qing dynasty official. The designer posted Trump donning her lacy black dress on her Instagram, praising her and writing that she "[radiates] with confidence, elegance and grace. A great example of the young and outstanding female image of America winning unanimous admiration across China."

While Donald Trump didn't consider that his family might appreciate what China has to offer for fashion, Tiffany's choice of designer for a night meant for her father to voice his ideology was perhaps slightly tone-deaf. It's also not the first time the younger Trump sibling supported Wang, as she was actually seated front row at the designer's show at New York Fashion Week. If that's not all, she's not the only Trump supporter to wear the brand. Per China Daily, Donald Trump Jr.'s fiance, Kimberly Guilfoyle, has also worn Wang's designs. "I wear Taoray Wang on my show on Fox News all the time," she declared in 2019.

That time she wore a matching outfit with Ivanka Trump

Who remembers when your mom used to dress you and your siblings in matching outfits for family pictures or the holidays?! We do, and it wasn't even cute back then. As a friend close to Tiffany Trump told Vanity Fair, the younger Trump sibling actually looks up to big sister Ivanka Trump when it comes to "politics advice, boy advice, and sisterly advice." As it turns out, Ivanka also dishes sartorial guidance, including teaching her what colors compliment her skin tone, and how to sit properly while wearing a dress. We actually can't blame Tiffany from taking tips from her sister; Ivanka's style is classy and iconic, even channeling a bit of "Jackie O" with her use of pearls and Chanel sets (via The Cut).

For their father's presidential inauguration, Tiffany and Ivanka Trump showed up wearing matching ivory and white pant suits. While both individually looked sophisticated, classy, and put together, the thought of matching with your sibling in your mid to late 30s didn't sit well with some. As The Cut noted, "Tiffany was clearly taking a page from Ivanka's playbook."

Her romper was so short, she had a wardrobe malfunction

Certain outfits that are cute (or appropriate!) for a beach vacation may not fare as well on the streets of New York City. Tiffany Trump found this out the hard way in 2017 as the Daily Mail paparazzi managed to catch her in quite the compromising position. Trump was caught sporting a tiny, short and strapless black romper to beat the summer heat. Yes, she was surely on her way to a beach in the Hamptons, but not before making a couple stops in NYC first. 

As she was getting into her SUV, Inquisitr noted that she got a bit "cheeky," revealing her activities in the Big Apple, including stopping at a newsstand to buy essentials for her trip, visiting a gym for a smoothie, and suffering an unfortunate wardrobe malfunction getting into her vehicle.

While we can admit Tiffany Trump looked amazing in her tiny black romper, perhaps it wasn't the most practical outfit for running errands in a big and bustling city.

Tiffany Trump was out partying with her mom in a see-through top

According to the Mirror, Tiffany Trump and her mother Marla Maples had an eventful evening in London, England, back in July 2018. Trump apparently began the evening in a stunning light blue suit; by the end of the night, the suit jacket came off, revealing her totally see-through blouse. Yikes! Maybe not the most appropriate when you're out partying with your mom!

Trump looked "worse for the wear," according to the Mirror, while exiting London's MKNY House in the wee hours; which is perhaps why she deemed it okay to remove the baby blue suit jacket to reveal the scandalous shirt in front of her mother, her security and the paparazzi. The blonde star most likely didn't enjoy the headlines made after her glam night out, and as a source close to Maples dished to People, Tiffany was already feeling out of sorts due to her father's "negative attention" as POTUS. "She's been having a rough summer," the insider shared, adding, "All the negative attention on her dad is stressing her out and she's just not been doing well lately."

While Trump's style is undoubtedly sophisticated and elegant, she still may need her big sister Ivanka to help with some self-awareness. We're rooting for you, Tiffany!