Tiffany Trump’s style has evolved over the years, but her outfits continue to be hit-or-miss. She’s been photographed wearing inappropriate ensembles for political events and normal outings, while certain looks just completely missed the mark. But Donald Trump’s youngest daughter scored only home runs during the inauguration weekend in January 2025 when she slayed formal maternity dressing. A day before her dad’s inauguration ceremony, Tiffany, who is pregnant with her first child with her husband Michael Boulos, donned a belted gray Zuhair Murad coat dress and black leather point-toed stiletto boots when she joined her family for a wreath-laying ceremony at Arlington National Cemetery in Virginia. She seemingly rewore the boots the following day, but this time paired them with a gorgeous floor-length navy blue coat dress for the inauguration. Tiffany ended the busy day looking stunning in an off-the-shoulder gray Zuhair Murad dress at the inaugural ball later that evening.

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However, Tiffany followed up her series of hits with yet another miss. A little over a week after the ceremony, she shared photos of herself seemingly channeling Sarah Huckabee Sanders while posing outside and in various rooms of the White House. Dressed in a dark red cape dress, opera-length black leather gloves, and what appeared to be the same stiletto boots she’d worn throughout inauguration weekend, Tiffany looked less first daughter and more TV series villain hatching some evil plot in the Oval Office. 

Trump supporters were all praise for Tiffany’s look in the comments section of her Instagram post, but some users noticed that her ensemble wasn’t entirely suitable for a happy occasion for the family. “When is your flight to Transylvania?” one critic commented. Another likened her look to the iconic deep red dresses and capes worn by handmaids in “A Handmaid’s Tale,” writing: “[Handmaid’s] Tale right there. Perfect fit.”

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Tiffany Trump donned a few leather looks during her party girl era, including a stunning short blue dress for the 2014 Mercedes-Benz Fashion Week, but in recent years, she has limited her leather items to just accessories and shoes. Unlike the first daughter, however, Sarah Huckabee Sanders has practically worn leather in all the ways she can over the years. Unfortunately, though she loves leather, it doesn’t seem to love her as many of her looks were total fashion fails. The Arkansas governor committed the fashion crime of pairing a brown leather skirt with knee-high tan suede boots for a Donald Trump campaign rally in November 2024. But even that wasn’t as bad as the shapeless brown leather dress and tan suede boots combo she wore to the Conservative Political Action Conference three months later. The terrible leather looks just kept coming as just weeks later, she was photographed sporting a tacky red leather dress featuring a bow that even Kimberly Guilfoyle likely wouldn’t add to her wardrobe.

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However, Huckabee Sanders may have started a trend in the Trump administration as Karoline Leavitt has also rocked leather a few times since being appointed White House press secretary. It might be because she’s Gen Z, but Leavitt has had a better track record when it comes to styling her leather looks. Her black leather dresses at a 2024 Donald Trump rally and the 2025 Super Bowl weren’t all that flattering, but she nailed incorporating the material in her daily style when she stepped out in a tight black shirt and leather pants, which she paired with a light brown jacket.