Tiffany Trump's Most Inappropriate Outfits

As one of Donald Trump's five children, Tiffany Trump has been under the mainstream spotlight from a young age, with the attention intensifying as her father became president of the United States. While most of the public's focus is reserved for Tiffany's professional endeavors and personal life, the world of fashion is equally interested in her style expression.

As a regular front-row attendee at major fashion shows, it's no surprise that Tiffany's fashion choices have garnered attention from critics, both positive and negative. According to a Vanity Fair report from 2017, Tiffany is pleasant to interact with at fashion events, but her personal style hasn't always been pleasant to witness, at least in terms of appropriateness.

Looking back, Tiffany's style has seen little evolution before and after her father's presidency, often leading to outfits that make her seem displaced in a sea of suits and dresses of appropriate lengths at political events. From looking like she was ready for the office while partying to the exact opposite, here are five times Tiffany's outfits completely missed the mark.

Tiffany's see-through top was wildly unsuitable for a public outing

Going out on the town can be a great way to let loose after a stressful day, but what one wears makes all the difference, particularly when they are the daughter of the president of the United States. In 2018, during Donald Trump's second year in office, Tiffany Trump attracted attention for her fashion choices as she exited a bar in London, England, sporting a rather inappropriate top.

Accompanied by her mother, Donald's ex-wife Marla Maples, as she strutted down the street, Tiffany donned a baby blue suit, suited more for a day at the office than a night of fun. However, it wasn't the choice of suit that raised eyebrows; rather, it was the completely see-through top she wore underneath. Other than the long-sleeved, high-neck blouse with black details simply not going with the rest of Tiffany's look, when your father is the president of one of the most watched nations in the world, it's hard to imagine how a sheer top would be a go-to for any type of public outing.

Underneath the unfortunate top choice, Tiffany opted for a flesh-colored bra, making things worse. While it's understandable that finding appropriate lingerie when one's shirt is sheer can be challenging, the choice of a nude bra gave the impression that Tiffany wasn't wearing anything beneath her see-through blouse.

Her bare legs stole all the attention at a White House Thanksgiving banquet

Who would have imagined that a suit was suitable for the bar while entirely baring your legs was reserved for Thanksgiving festivities? Well, it's what Tiffany Trump evidently believes, as she chose to wear a super short tweed coat sans bottoms at the 2017 Thanksgiving Turkey pardoning ceremony held at the White House. Alongside her half-sister Ivanka Trump and niece Arabella, Tiffany decided to make an eyebrow-raising fashion statement (or maybe she simply forgot her pants).

While Ivanka sported a similar outfit, her approach was entirely different. Despite her peacoat being the same length as Tiffany's, Ivanka opted to add a skirt and full-coverage tights. Even though a presidential family doesn't need to adhere to strict fashion rules, like the British royal family for instance, wearing an almost micro-mini length coat without any other visible clothing garment is undoubtedly an inappropriate choice. Tiffany accessorized her red-pink ensemble with black pointy-toe pumps, a pink clutch, and understated jewelry.

Interestingly, Tiffany's coat is much more affordable than Ivanka's Dolce & Gabbana one, priced at almost $3,000. Designed by women's fashion label Chocheng, Tiffany's short tweed piece can be purchased second-hand for just under $40 on The RealReal. Just don't forget to wear something underneath it, perhaps.

Tiffany went full Y2K in the worst way possible

Tiffany Trump wore another questionable look in 2017, but this time, it wasn't her bare legs that were the problem. Do you remember those early 2000s paparazzi photos of celebrities leaving clubs all disheveled, wearing outfits teetering on the edge of wardrobe malfunctions? Unfortunately, that's exactly what Trump looked like ahead of Philipp Plein's New York Fashion Week runway show.

Trump's outfit for the event featured so many bad elements that it's hard to pick a single one. The black bodycon mini dress, given its already short length, would have likely looked much better had it not had cutouts along the bottom and down the arms. Adding to the style faux pas, the bottom cutouts were adorned with the designer's name in glitter, while the top arm cutouts featured a chunky gold charm on both sides, contributing to an overall tacky vibe.

As if all of the above wasn't enough drama for the little black dress, Trump opted for black pumps featuring silver glitter details and a studded black leather clutch. She went with a heavy smokey eye makeup look and a hairstyle that evoked memories of the "bump it" trend. While one might argue that the outfit wasn't inherently inappropriate for the occasion, it certainly missed the mark in terms of fashion, especially considering Trump's affluent background.

She looked like she was going to the club on election night in 2016

Tiffany Trump's perplexing fashion choices made an appearance on election night in 2016, when her father, Donald Trump, was voted the 45th President of the United States. While the rest of her family opted for outfits suitable for the occasion, such as suits, pantsuits, and more modest dresses, Tiffany stood out in a blue satin mini-dress paired with nude pumps, giving off a vibe more fit for a club than a political event.

It's worth noting that Tiffany's half-sister, Ivanka Trump, sported a similar outfit, a short blue dress, though with a different aesthetic. Ivanka opted for a pleated skater dress by Alexander McQueen, featuring a much fuller bottom compared to Tiffany's flat A-line dress. While Ivanka's look also completely missed the mark for the occasion, at least she didn't look like she took a wrong turn on her way to a night out and ended up on a national stage.

The inappropriate length and the shininess of Tiffany's dress made it difficult to ignore, but at the same time, it gave the impression that she put minimal effort into dressing up for such a big night for her family. A change in hairstyle or opting for a longer version of the garment could have easily elevated Tiffany's look for the special occasion. Instead, her high-end party look lives forever on the internet.

Tiffany's White House outfit looked like a weird costume

When visiting the White House as a family member of the president, the dress code surely doesn't call for a ball gown or similarly glamorous attire. Still, Tiffany Trump's 2020 outfit erred on the side of satirical. While the Trump family isn't exactly known for expressing themselves through clothing, except for Melania Trump and her outrageous fashion choices, it's safe to say that Tiffany's ensemble reflected her personal style.

In a photo shared on Tiffany's Instagram, she's seen standing in a room at the White House wearing a short-sleeved knit top with a high neck, eerily reminiscent of the 1940s, paired with black skinny jeans. While the combination isn't inappropriate per se, her footwear choice stole the show in the worst way possible.

Tiffany opted for pointy ballet flats featuring the American flag in glitter, made by the Italian luxury brand Aquazzura. The flats were likely limited edition, as they're no longer available on the brand's website (they once retailed for $435). With the rest of her outfit maintaining a subdued aesthetic, the bold shoes seemed wildly out of place. Instead of complementing her look, they made Tiffany look like she was trying to put together a patriotic costume from items in her closet. "Get a stylist," one Instagram user pleaded under her post. Adding to the peculiarity of Tiffany's footwear choice, the same Italian brand had previously sued Ivanka Trump for trademark infringement in 2017.