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Ivanka Trump’s 12 Most Questionable Fashion Choices 

Ivanka Trump’s style has always sparked conversation, both for its elegance and for some of the more controversial choices she’s made throughout the years. As a woman in the public eye—first as a fashion designer and model, and then as the First Daughter—Ivanka’s outfits have occasionally left a lasting impact, not for the right reasons. From eye-popping displays of wealth to ill-timed outfits amid national crises, her wardrobe has at times turned heads for all the wrong reasons.

Ivanka’s own approach to fashion, once founded on the principles of modesty and professionalism, took a noticeable shift when her father entered the political arena. What was once seen as simply fashion quickly evolved into something much more complicated—an extension of her family’s controversial brand. While some may have thought her clothing choices were intended to project professionalism, others saw them as an attempt to market herself and her business in a deeply public, sometimes inappropriate, manner. Let’s explore some of the moments when Ivanka’s outfits caused as much of a stir as her political influence.

1. Oversized Sleeves Steal the Spotlight in Colombia

Ivanka Trump’s December 2019 trip to Colombia, where she was promoting her Women’s Empowerment Initiative, was supposed to be a moment for her to highlight important issues regarding women’s rights and economic empowerment. However, her appearance quickly became overshadowed by an unexpected fashion mishap. Ivanka wore a striking $1,650 Johanna Ortiz dress, featuring large, billowy sleeves that were designed to make a bold statement. While the dress itself was eye-catching, it was the dramatic sleeves that stole the show. During a photo session with Colombian and U.S. officials, a sudden gust of wind caused the sleeves to flutter wildly, turning them into the center of attention.

Instead of focusing on the significant work she was doing in Colombia, the media coverage was dominated by the unpredictable movement of her sleeves. As they billowed out uncontrollably in the wind, the attention shifted away from Ivanka’s message of empowerment to the fashion blunder. The moment became a viral sensation, with many on social media pointing out how the extravagant dress became more of a distraction than a symbol of the cause she was promoting. While her initiative was intended to help women in developing countries, the dramatic sleeves seemed to steal the spotlight, leaving many questioning whether her fashion choices overshadowed the purpose of her visit.