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Who Is Fashion Stumping For in 2020?

While the Democratic nomination is still very much up for grabs, industry insiders are already showing public support for their favourite presidential candidates — and sometimes even taking things a step further.
(L-R) Derek Blasberg with Michael Bloomberg; Emily Ratajkowski endorsing Bernie Sanders; Anna Wintour with Mayor Pete Buttigieg | Sources: Instagram @derekblasberg; Instagram @emrata; Getty Images
  • Lauren Sherman

NEW YORK, United States  — As head of fashion and beauty partnerships at social media platform Snap, Selby Drummond has one of the most coveted positions in the industry. But that hasn't stopped her from taking a leave of absence from the role in order to work for former New York Mayor Michael Bloomberg's presidential campaign.

"My mother taught me that the democratic process requires more of us than pulling a lever once every four years," Drummond said in a statement to BoF. "I joined the campaign and the candidate that I believe has the greatest chance of beating Donald Trump in November. We will all of course unite behind the eventual nominee, but right now we must do whatever we can to help the candidate we believe in the most."

Drummond may be a unique example, but she is not the only fashion insider making an early bet on a Democratic candidate, as the race leaves the chaotic Iowa caucus behind and looks toward Tuesday’s primary in New Hampshire.

Designer Rosie Assoulin and her friend, the writer and Man Repeller founder Leandra Medine, have mentioned Bloomberg on Instagram, as has YouTube's head of fashion and beauty partnerships, Derek Blasberg. American Vogue Editor-in-Chief Anna Wintour and Broadway executive Jordan Roth have fundraised for former South Bend, Indiana, Mayor Pete Buttigieg. Last summer, Tom Ford said he offered to style Buttigieg on the campaign trail. The candidate declined.

Former Out Editor-in-Chief Phillip Picardi, who backs Elizabeth Warren, said he chose to publicly endorse the Massachusetts senator after he left the magazine in December because he knew he would no longer be covering the campaign. He said Warren's preparedness, anti-trust policies and ocean conservation effort are among the reasons he is backing her.

“A lot of people who I knew and worked with were already working for and even helping the campaign,” he said.

On Friday, Buttigieg remained virtually tied with Bernie Sanders in the Iowa delegate count. (Technical issues have delayed final results, which may never surface.) The 38-year-old former mayor and the 78-year-old Vermont senator were followed in the caucus results by Warren, while former Vice President Joe Biden, long thought to be the safe move by Democrats who fear the other candidates are too progressive or inexperienced to beat President Donald Trump, had underperformed, locking zero delegates.

For fashion, the biggest question mark is who will win Wintour's allegiance.

Bloomberg, who did not participate in the caucus but instead staged a rally in Detroit, the largest city in the key swing state of Michigan, is gaining traction with New Yorkers who believe he’ll play nice with big business and has the financial resources to out-campaign Trump. However, critics have resurfaced his “stop-and-frisk” policing policy as mayor, citing it as a major concern.

The Gen Z crowd is favouring Sanders, who remains a symbol of progressive dissent, although his attitude toward Warren — CNN reported that he said he didn't believe a woman could win — and concerns about his age and physical health have even some far-left voters feeling cold.

The disarray reflects a Democratic party even more deeply divided than in 2016, when Hillary Clinton beat Sanders for the nomination and won the popular vote in the general election, but was defeated in the electoral college by Trump.

For fashion, the biggest question mark is who will win Wintour's allegiance. The Condé Nast artistic director pushed hard for Clinton in 2016, ushering in an era of lifestyle publications endorsing candidates. (There were also reports, as there had been during the Obama administration, that she was interested in being appointed ambassador to the United Kingdom.)

While Wintour has shown early support for Buttigieg, hosting a fundraiser for him at her home in the winter of 2019, she has not publicly endorsed anyone and is unlikely to do so until a frontrunner emerges, according to a source familiar with her thinking.

In any case, the world will be watching.

“The primaries are a good time to sit back and enjoy the show,” Picardi said. “Where fashion can be helpful is with voting efforts. The only way we are going to win is if we overwhelm the polls and out-organise.”

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