Who Wore it Better? Politicos vs. Fashion Icons

Politicos pull out the big guns to take on fashion icons in a clash of posh proportions. Who wore it better? You decide.

Round One: Trench Warfare

Anna Wintour vs. Nancy Pelosi

After wrapping a meeting in the White House before the looming government shutdown—at which POTUS remarked, “If we don’t get what we want... I will shut down the government”—Speaker of the House Nancy Pelosi shut down questions about her style with this red Fire coat that Max Mara decided to reissue for 2019 after photos of Pelosi wearing the power piece went viral. Anna Wintour is a formidable fashion foe who fought her way to the top global style scene for wearing statement pieces like this off-shoulder pastel-blue coat.

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Round Two: Asymmetric Attack

Rosa DeLauro vs. Iris Apfel

As the ranking member on the Labor, Health and Human Services, and Education Appropriations Subcommittee, Connecticut Congresswoman Rosa DeLauro oversees the nation’s investments in education, health and employment. She also overlooks the most adventurous and diverse closet on the Hill. Meanwhile, as the ranking member of eclectic American style, 97-year-old interior designer and fashion icon Iris Apfel lords over a closet of unending mix-and-match combinations that is the envy of armies of influencers.

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Round Three: Frontal Assault

Ted Cruz vs. The Most Interesting Man Alive

After fending off trendy challenger Beto O’Rourke in the 2018 Senate elections, the junior senator from Texas decided to add some Austin hipster flair to his image by growing a well-groomed beard. He’d certainly look more interesting reading Green Eggs and Ham from the Senate floor now like he did during the 2013 government shutdown. Meanwhile, would The Most Interesting Man Alive still be a cultural icon with Lone Star State-sized ambitions without his seminal coiffed mane? Doubtful.

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Round Four: Boot Camp

Kanye West vs. Melania Trump

If business mogul Kanye West wanted to walk back any of the comments he made in his televised Oval Office tête-à-tête with President Trump—which covered the 13th Amendment, North Korea, mental health and MAGA hat-wearing superpowers—he could do so in these Yeezy 950 duck boots ($585). The first lady uses style to make statements, too—remember that $39 “I Really Don’t Care. Do U?” Zara jacket? If these Timberland premium waterproof boots ($140) could talk they’d say, “I can weather any storm.”

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Round Five: Marching Orders

Ivanka Trump vs. Gigi Hadid

Stepping out like a boss comes naturally for adviser to the president/first daughter Ivanka Trump. Whether she’s color-coordinating her family’s outfits to match Air Force One or helping Treasury Secretary Steven Mnuchin choose the next leader of the World Bank, she rocks her powerful platform. Fashion is family business for “it” girl Gigi Hadid, too. Like her sister Bella Hadid, she always turns heads with keenly orchestrated sartorial selections—mini wrap dress and thigh-high suede boots? Razzle dazzle.

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