Tiffany Trump's Most Inappropriate Outfits To Date

Although Tiffany Trump spent most of her childhood away from dad Donald Trump, she has become a firm fixture within the Trump clan, often standing alongside her father and siblings at public events. Unfortunately, no one is immune to making the odd fashion faux pas, and Tiffany has found her clothing the subject of speculation on numerous occasions.

In an effort to shake up her style, it was reported that Tiffany had enlisted the help of famed stylist Phillip Bloch to help her dress for her father's inauguration. Since then, not only has she debuted a new, more mature look that has everyone talking, but she also tied the knot with Michael Boulos in a wedding at Mar-a-Lago on November 12, 2022. Plus, Tiffany's experience in law school and graduating in 2020 has likely influenced her career prospects and approach to politics and her public image.

But all of this hasn't stopped Tiffany from being critiqued for wearing so-called inappropriate outfits at official events and in photos posted on her social media. From unusual White House ensembles to questionable Instagram outfit uploads, these are her most inappropriate outfits to date.

Visiting the United Kingdom from the United States is always a treat, especially when Buckingham Palace is involved. In June 2019, the Trump family was invited by the late Queen Elizabeth II 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!

Well, this is awkward. As Tiffany Trump's father, Donald Trump, 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.

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 didn't consider that his family might appreciate what China has to offer for fashion, Tiffany's choice of designer on a night meant to highlight her father to and his ideology could he seen from his and his supporter's perspectives as 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 fiancé, 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.

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.

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."

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," recounting 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 she looked amazing in the black romper, perhaps it wasn't the most practical outfit for running errands in a big and bustling city.

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. 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.

She most likely didn't enjoy the headlines made after her glam night out, and as a source close to Maples dished to People, Trump 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 Trump, to help with some self-awareness. We're rooting for you, Tiffany!

In November 2017, Tiffany Trump attended the annual pardoning of the National Thanksgiving Turkey at the White House alongside sister Ivanka Trump. While the siblings both wore red coats, Tiffany's outfit had a lot of people asking if her fashion choices were appropriate for the official occasion she was attending. In particular, Tiffany's super short coat made it unclear whether she was supposed to be wearing anything underneath. This pantless look was made even stranger considering the fact that it was November, meaning that Donald Trump's daughter was likely subject to the winter chill at the outdoor event. 

Critics on X, formerly known as Twitter, appeared to be outraged by Tiffany's ensemble, particularly when it was compared to Ivanka's more staid look, which included a pair of black pantyhose. "THAT'S TOO SHORT, LOOK AT THE BACK, TIFFANY," one X user wrote in response to the outfit. Someone else critiqued the coat, writing, "The only thing my family could agree on this Thanksgiving: Tiffany Trump's attire at the turkey pardon was not good." However, not everyone agreed that Tiffany's outfit for inappropriate for the occasion at hand, with one fan writing, "She's got nice legs why hide them." While opinions were mixed, it's clear that Tiffany's turkey day ensemble was a conversation starter.

Melania Trump has worn some controversial outfits, and her stepdaughter appeared to have followed suit. In November 2017, Tiffany Trump surprised her fans when she shared a photo of herself wearing an all-nude dress, consisting of a sheer pleated mini-skirt and a lace top over a skin-tone camisole. While Trump didn't caption the picture, her followers had a plethora of opinions, both good and bad, and they weren't afraid to express them.

One user commented on the Instagram photo, writing, "your telling me you looked at this picture before posting it and you still decided to post it." Another shared their very strong opinion about the outfit, writing on the platform, "Does she not know that she needs to show some respect responsibility and intelligence. Because it certainly looks like that showing parts of her that should not be showing. That don't look good on our country." While it's perhaps unfair to suggest that Tiffany shared the responsibility of the presidency with dad Donald Trump, it's clear that her nude outfit was provocative to some.

Luckily, Tiffany also received some positive responses to the unusual outfit, with many fans commenting with heart emojis and compliments. But considering the mixed reactions to her look, Tiffany's sheer, nude mini-dress remains one of her most inappropriate and potentially controversial outfits.

In February 2019, President Donald Trump delivered his State of the Union address, and Democratic women decided to send a message during the event. In honor of the 100th anniversary of the 19th Amendment, female House Democrats donned white outfits to pay tribute to the suffragettes who fought for women's right to vote. The decision to wear white was also reportedly viewed as an opportunity to oppose some of the then-president's political policies. Hence, it came as somewhat of a surprise when Tiffany Trump appeared alongside her Republican family members wearing an all-white outfit.

While Tiffany didn't comment on her decision to wear a white dress for the event, onlookers questioned whether she was actually sending a not-so-subtle message in support of the Democrats. One X user said of the look, "Tiffany Trump wearing suffragette white to the #SOTU is the subversive Trump family member we all need. Write a book Tiffany! Take the whole ship down." Another commentator wrote on X, "Tiffany Trump wore suffragette white last night, matching the House Democrat women and Speaker Pelosi. I hope she's sending a message."

We may never know whether or not Tiffany's choice to wear white at the State of the Union was intentional. Still, while she was praised by some, her outfit was likely found to be inappropriate to the people who tend to disagree with the Democratic women of the House.

In March 2020, Tiffany Trump shared a photo taken inside the White House, and although her outfit shouldn't have caused any furor, onlookers had questions about the look. In the demure picture, Trump can be seen wearing a pair of fitted black pants, a high-neck cream top, and a pair of flat pointy shoes from the designer Aquazzura. Despite looking perfectly respectable in the picture, some commenters were extremely mean about the business-like ensemble. "Your feet are huge," one person commented on the Instagram post. Another person wrote, "Honey you look like a limp noodle," while yet another onlooker dramatically declared, "cursed image."

The law school graduate also received plenty of heart emojis underneath her upload, but they couldn't negate the awful things being said about her outfit and choice of pose. While it's largely unclear why her casual White House look was so inappropriate or offensive to so many people, it would seem that the simple combination was somewhat out of character for the former president's daughter.

Election night in 2016 was an important occasion for the Trump family. Tiffany Trump appeared alongside the rest of her family at the New York Hilton Midtown in Manhattan, where Donald Trump gave his acceptance speech after winning the presidency. Tiffany twinned with her sister, Ivanka Trump, at the event, with both wearing short blue dresses. However, Tiffany's outfit looked a little out of place at the official event, particularly as the mini-dress was made from a shiny satin material, and featured sparkling adornments at the neckline.

While Tiffany wasn't totally to blame for the criticisms leveled against the Trump family's fashion choices, her party dress did little to dissuade the naysayers. For instance, The New York Times declared that Donald's win would usher in an unfashionable period in the White House, in stark contrast to the respect Michelle Obama regularly garnered from designers and publications.

Sadly, during election season, Tiffany didn't receive much praise from her father, despite him openly praising her siblings during an interview with "Fox and Friends" (via Express). "I'm very proud, because Don and Eric and Ivanka and — you know, to a lesser extent 'cause she just got out of school, out of college — but, uh, Tiffany, who has also been so terrific," he stammered. "They work so hard." Perhaps the fact she's not Donald's favorite child has contributed to some of the criticism from his fans over her fashion choices.