Tiffany Trump Outfits That Just Didn't Work

As Donald Trump's youngest daughter, Tiffany Trump has been in the spotlight her whole life. She was introduced to fashion from a young age thanks to her businessman dad and uber glam mom Marla Maples and that meant being photographed in fabulous outfits before she could even walk. Even as a child Tiffany got glam for Donald's notorious Mar-a-Lago parties. But, despite decades rubbing shoulders with the most fashionable socialites, just like her half-sister Ivanka Trump, Tiffany has a few outfits in her back catalogue that didn't work.

That's understandable seeing as the former first daughter is known for her love for fashion, meaning she's not shied away from clothing risks. In fact, she's so dedicated to keeping abreast of the latest styles she took time away from her studies to attend a few New York Fashion Week events in 2017. "I can't go to many shows. I'm in law school now, so realistically I have a lot of work to do," she told The Cut. "I am going to a couple places where I know the designers personally, and supporting them." Only, there are a few times Tiffany could have done with a little help from her designer pals.

Philipp Plein has created some gorgeous, classy designs — but the LBD Tiffany Trump wore to his 2017 New York Fashion Week show, unfortunately, wasn't one of them. The black mini-dress featured embellished logo bands around the thighs and long sleeves with multiple cut-outs. The sheer panels, though glitzy, meant Tiffany likely showed more than she bargained for when she sat down. We think this dress would have been more appropriate at midi length or with a black leather-look jacket to balance the cut-outs. Still, we give her props for expertly matching her shoes to her dress.

There's nothing wrong with showing leg, and we admire that Tiffany Trump has the confidence to wear what she wants. When she attended the Thanksgiving Turkey Pardoning Ceremony in 2014 though, her short ensemble made her stand out in the wrong way. She wore a red marl coat that covered everything but her bare legs and black pointed-toe pumps. It didn't work because her family dressed warmer. Ivanka Trump, meanwhile, sported a red coat with a floral dress and opaque black tights. We're not suggesting Tiffany take fashion cues from others if they don't feel authentic, but co-ordinating with her kin would have resulted in a more appropriate outfit for the formal event and the weather. One X, formerly known as Twitter, user even tweeted, "Anything that short should be worn [with] tights and not at [the White House]."

Tiffany Trump looked glamorous in a plunging, form-fitting, bandage champagne top in a 2018 Instagram upload. However, her choice to pair it with skinny black pants, a structured blazer over the shoulders, and flats didn't work. The glam top was fit for a club or red carpet, but her comfortable loafers and sensible backpack looked more like she was heading to a library. We'd have recommended swapping the pants for a black pencil skirt, which was trending at the time, and wearing a trendy neutral court shoe for a more cohesive look.

Boxy crop tops and high-waist, A-line skirts were all the rage in 2014, but there's a reason this trend was left there. We appreciate that Tiffany gave the trend a go, seeing as, according to her Instagram post, she was on her way to a New York Fashion Week show (where better to take a fashion risk?). However, as shown in the photo, when she turned to the side, the pink top added bulk in the wrong places for an unflattering silhouette. Plus, because the top was so billowy, it created the risk of a wardrobe malfunction. A classic, fitted top would have been chicer, as would a crop top and oversized pants.

Tiffany Trump made another fashion misstep in London back in 2018 by wearing two pieces were made for two different occasions. In this case, her high-neck, long sleeve black top totally clashed with her pastel blue pantsuit. The top was suitable for a night at the bar, while the two-piece was better for the office (she was actually leaving the members-only club The Arts Room with her mom). Tiffany's bag for the evening was quite the odd choice, too. The sparkly, holographic box clutch didn't match any part of her outfit and also didn't work as a pop of color. However, it could have if she'd opted for a darker suit.