Tiffany Trump Outfits That Completely Missed The Mark

Tiffany Trump's relatively under-the-radar existence drastically changed when her father, Donald Trump, decided to run as the Republican candidate for president. The then-unknown Tiffany, whose mother Marla Maples raised her in California after she and Donald divorced, was thrust onto the national stage. There was suddenly speculation about everything about her, from her relationship with her half-siblings, Donald Jr., Ivanka, Eric, and Barron Trump, to her relationship with her father to her most inappropriate outfits.

Tiffany, who graduated from Georgetown Law School in 2020, had an interest in fashion after an internship at Vogue, but that fell to the side as she pursued law instead. But that doesn't mean her interest in fashion disappeared. Tiffany often attends fashion shows with Maples and has hinted that she's following in fashionista Ivanka's footsteps by posting more fashion-forward looks of herself on Instagram. However, some of the outfits she's worn have completely missed the mark. Maybe the law was a safe gamble. Her father said he was glad to have a lawyer in the family, after all.

Half-sisters Tiffany and Ivanka Trump, along with sister-in-law Lara Trump, were among the Trump family members at the 2016 Republican National Convention, held in July in Ohio. Lara looked chic in black and white separates, while Ivanka looked the part of the conservative style icon in her floral skirt and coordinating sweater. Little sis Tiffany missed the mark, however. At the time, Tiffany was a 22-year-old who had just finished at the University of Pennsylvania and was interning at eyeglass brand Warby Parker.

For this event, the recent grad wore a fitted white lace dress, topped by a cream sweater-jacket. Just like combining black and brown or black and navy, wearing cream and white together is a long-debated topic. While some vow that the pairing is a fashion no-no, others think it can work. Unfortunately for Tiffany, the look fell flat. Combining white and cream can look very sophisticated, but only if it's done with elegant pieces. If Tiffany had worn more refined pieces, this look could have worked better.

In 2018, during Donald Trump's first presidency, former party girl Tiffany Trump hit the town in London. She was photographed leaving the members-only Arts Club, heading to hotspot MNKY HSE, a Latin American restaurant and club in the swanky Mayfair neighborhood. Is this the outfit we'd hit the town in for a night out in London? Not so much.

This ensemble hit some seriously tragic notes. Let's start with the sheer top with the nude bra underneath. It's a bit late to start teaching lessons in class to the Trump clan, but surely the president's daughter should know better than to wear a see-through top? Then there's the ill-fitting suit. A suit is work wear, not our top choice for hitting hotspots. Even the brown box clutch felt wrong; a black or nude one would have worked better here. But to be honest, the handbag is the least of our worries with this horror show.

No stranger to living an insanely lavish life, Tiffany Trump ventured to the French Riviera in May 2019. She was just one of the famous faces gracing La Rue de la Croisette then for the Cannes Film Festival. The outing caused a controversy, as it was reported that taxpayer money helped fund the trip for Trump and her Greek billionaire boyfriend (now husband), Michael Boulos. 

The two hit the AmFar gala and later posted pics of themselves with Chris Tucker and Jonathan Cheban. Trump also posted a photo of herself crossing the famed seaside Cannes boulevard wearing a confusing satin dress that looked like it could've been a dressing gown. The high-low style appeared too long in the back, and the bust came together in messy ties. It goes without saying that this outfit was not among Trump's greatest triumphs, nor was the trip as a whole, at least not in the eyes of the U.S. public.

Tiffany Trump was looking fashionable and pulled together for the January 2020 State of the Union address at the U.S. Capitol, where father Donald Trump addressed the nation. The trouble was her stylish look didn't fit the occasion. Though she was nowhere near as offensive as those on our list of worst-dressed attendees at the 2025 joint address, Tiffany's outfit still failed to impress. 

This ensemble would have been perfectly fine if it had been for a spring Easter outing, for instance. Instead, it missed the mark. Why? For one reason: the color. She went for a light shade of blue shade, which she also leaned into for her wedding to Michael Boulos, where she had bridesmaids, including Ivanka Trump, wearing the hue. We wonder if she loves the shade as a nod to Tiffany & Co., the famed N.Y.C. jeweler that served as inspiration for her name. While it's a perfectly lovely color, the pastel hue didn't feel right for the middle of winter in D.C. The accessories didn't deliver, either. The white bag would have been better for a luncheon fundraiser at Mar-a-Lago. And the sparkly heels? Nothing about them screamed serious political event in chilly January.

As her father was furiously signing executive orders in the Oval Office on January 21, 2025, first daughter Tiffany Trump was serenely posing on the grounds of the White House before she and the rest of the Trump family members attended the National Prayer Service at the Washington National Cathedral in D.C.

Nothing says attending a prayer service at church like opera-length leather gloves and black boots, right? Again, the outfit was actually beautiful, but it completely missed the mark because it wasn't appropriate for the occasion. Dressing like a villain from a Disney live-action film isn't the way we'd go for such an event. Instagram trolls commented on Tiffany's post of herself in this look, also finding the character resemblances. One wrote, "What in the handmaids tale is this?!" and another added, "When is your flight to Transylvania?" Despite her stunning transformation, it seems that Tiffany just can't catch a break. But we don't doubt she'll continue to try.