On Tuesday, Anna Wintour, the Vogue editor who holds sway over much of the U.S fashion industry, is expected in Chicago, where she and supermodel Iman will join President Obama’s campaign manager, Jim Messina, for a night of stumping. For $1,000, donors can schmooze, shop and pose for photos with the storied editor.

Two days later, Wintour and Sarah Jessica Parker are planning to host a $40,000-a-plate fundraising dinner with the Obamas at Parker’s New York home.

The two high-priced, high-profile events put the spotlight on a symbiotic relationship developing between the Obama campaign, with its style-conscious first lady who dons a wide variety of American designers, and a deep-pocketed, largely Democratic fashion industry, which has been increasingly coordinating its support of Obama.

In February in New York, right before Fashion Week, Wintour and actress Scarlett Johansson hosted a fundraiser for the launch of the campaign’s Runway to Win online store and “project by fashion designers in support of Obama 2012,” which sells scarves, T-shirts and wristlets created by 22 designers to raise money for the reelection effort. After the success of the 2008’s Runway to Change site, which raised more than $1 million, the campaign is putting stock in fashion-forward initiatives.

Deep-pocketed assistance

Name an American designer. Vera Wang. Michael Kors. Diane von Furstenberg. Michelle Obama wears these American luxury labels and a host of others, earning her consistent praise from a fickle industry. She knows the tailoring of Narciso Rodriguez, the flounce of Marchesa, the sweetness of a Tracy Reese sheath.

Her sartorial savvy hasn’t hurt her husband. With Michelle Obama’s style, a socially progressive political agenda and a campaign ready to promote top designers at fundraisers, the industry coalesced behind the couple in 2008. This year, the designers behind many of the labels hanging in the first lady’s closet are supporting her husband’s reelection campaign, hosting high-dollar fundraisers and making campaign contributions. Although fashion industry executives have donated to both parties during past election seasons, designers traditionally supported issues, such as AIDS and the environment, rather than candidates. Obama is the first presidential contender who has generated widespread and deep-pocketed support from them.

A look at every American designer label Michelle Obama has worn since 2008, according to Mrs-O.com, a fashion blog that tracks the first lady’s daily wardrobe, indicates that many of her favored designers support the president. Excluding jewelry designers and mass-market retailers, nearly 50 percent of American designers worn by Michelle Obama donated to her husband’s 2008 or 2012 campaigns, according to Federal Election Commission filings. By early June 2008, only a handful of these designers had donated. In comparison, the number of designers donating by June 2012 has tripled.

In contrast, none of the American apparel designers worn by the first lady during her husband’s first term have donated to Republican candidates in 2008 or 2012. And according to a study by the nonpartisan Center for Responsive Politics, fashion industry executives and employees in 2008 contributed almost twice as much to then-candidate Obama as to the GOP nominee, Sen. John McCain.

The first lady’s campaign spokeswoman Olivia Alair said: “The first lady thinks that women should wear whatever makes them feel good and be comfortable. That’s how the first lady chooses her own clothes and based on no other considerations.”

Michelle Obama has been heralded by the industry for promoting fashion in a different way than her predecessors. Previous first ladies have worn American designers proudly, but most followed the couturier model of having a few chosen designers make their clothes. Jacqueline Kennedy famously wore Oleg Cassini, ruffling feathers with her preference for French labels. Nancy Reagan, faithful to American designers including James Galanos and Oscar de la Renta, waded into controversy and undermined her own efforts to branch out and embrace American fashion by borrowing clothing and jewelry from designers. Michelle Obama has learned from the missteps of first ladies past, seeking out up-and-comers and wearing more than 50 American designers in her husband’s first term. She has also mixed high-end labels with moderately priced pieces from stores such as J. Crew and Talbots.

Those looking for patterns would be hard-pressed to find any. No single designer can claim a hold on her wardrobe, nor does giving to the campaign guarantee a coveted place in her closet. Some designers have become first-time donors this year after having their designs worn by the first lady. But other big givers are not staples of the Obama closet, and some who have gotten a big boost from the first lady haven’t given at all.

●Barbara Tfank, who designed Obama’s dress for a visit to Buckingham Palace in 2011, did not donate to the 2008 campaign but has since donated $5,000, the maximum for the 2012 cycle.

●High-dollar donor Tory Burch did not donate in 2008 but has since given the maximum $30,800 to the Democratic National Committee and the maximum $5,000 to the campaign. Burch’s blog shows Michelle Obama wearing a pair of her chain-trimmed boots, but Burch’s designs are not a staple of the first lady’s wardrobe.

●Jason Wu, who designed Obama’s inaugural gown and much of her subsequent wardrobe, has not donated to the campaign, although he is participating in the Runway to Win initiative.

●Reed Krakoff, the designer of the controversial $990 falcon blouse worn by Ann Romney, donated $3,000 to the 2008 Obama campaign.

Sometimes, Michelle Obama appears to choose designers simply because they’re present at events. The first lady wore Donna Karan publicly for the first time to a DNC fundraiser that the designer hosted in 2010.

Similarly, Obama wore a dress from donor Georgina Chapman’s Marchesa line to the British state dinner that Chapman and her husband, Harvey Weinstein, attended.

Simon Collins, dean of fashion at Parsons the New School for Design, says the industry support doesn’t stem from Michelle Obama’s patronage, but rather from the Obama administration’s eagerness to embrace fashion in ways previously not done.

Economic impact

“Clearly, both the administration, and by extension the first lady, made a decision that they would be public in their support for fashion — so, we’re in. We want to support them,” Collins said. “For those who say it’s just Michelle, frankly, it trivializes the attention the administration is paying to our industry.”

Steven Kolb, chief executive of Council of Fashion Designers of America, says designers are organizing because they support the president’s policies.

“When people are looking at who he is and lining up to support him or not, it has to do with their own personal beliefs,” Kolb said. “Social issues they think are important, such as same-sex marriage, his policies and positions on Afghanistan or what he’s done in terms of economic recovery.”

Prabal Gurung, who is participating in Runway to Win but who has not donated to the campaign, said the president’s backing of same-sex marriage has deepened his support for him.

“I was already sold on him, but his recent support for gay marriage took courage,” the designer said.

But there’s no doubt that being worn by the first lady gives designers — and their companies — a boost.

David Yermack, a professor at New York University’s Stern School of Business, examined Michelle Obama’s 189 public appearances between November 2008 and December 2009 and found that the appearances coincided with spikes in the stock prices of the companies whose clothes she wore. Yermack’s analysis says a single appearance by the first lady can generate $14 million in value for a company.

At a fundraiser held months before the 2008 election, designer Tracy Reese met the would-be first lady. “She gave me a big hug and said, ‘I’d love to be wearing your things,’ ” Reese recalled. Reese donated to the Obama campaign in 2008 and 2012. After Michelle Obama wore Reese’s raspberry-colored lace dress on the cover of People in April 2009, interest in her line soared.

“I definitely saw a sales spike, particularly in the styles she’s photographed in,” Reese said. “I think everybody loves the idea of being able to wear something she’s wearing.”

While the Obama campaign has embraced designers, Vogue and its editor have helped to organize them. In 2008, Vogue staff members Luisana Mendoza and Sylvana Ward Durrett developed the idea for a designer campaign store, and the Runway to Win model — called Runway to Change four years ago — was born. The duo came up with a roster of designers after working with campaign officials. “And Anna, of course,” Mendoza said. “Just to be clear, this is not a Vogue initiative. It’s an Anna Wintour project.”

With Wintour’s guidance, they recruited designers and chose the 25 participants — a mix of established designers and newcomers. The store launched in September 2008 and raised more than a million dollars in the few months before the election. (The campaign launched the 2012 store in February, giving supporters an opportunity to buy earlier.)

En Vogue

Ward Durrett, who is now Vogue’s director of special events, said the goal was to galvanize the growing ranks of fashion-savvy young voters: “At the time, young people were responding to the world of fashion. Designers are becoming celebrities now.”

The 2008 campaign marked Wintour’s first public foray into presidential politics. According to the Obama campaign, she is a top bundler, raising more than $500,000 for the Obama Victory Fund. (Wintour’s spokeswoman was unaware of the exact figure, and Wintour declined to comment for this article.) In 2010, she hosted an intimate affair to benefit the DNC at her New York townhouse, where designers including Marchesa’s Chapman and Diane von Furstenberg paid up to $30,400 to attend. In addition, she has attended high-profile White House events, including two state dinners, and she serves on the President’s Committee on the Arts and Humanities.

Last Friday, the Obama campaign released a video of the Vogue editor wearing a $95 Thakoon Runway to Win silk scarf. “I’m so lucky in my work that I’m able to meet some of the most incredible women in the world: women like Sarah Jessica Parker and Michelle Obama,” she says, before inviting viewers to enter a raffle for a chance to attend dinner with the first couple at Parker’s home.

The Republican National Committee responded quickly, issuing a video criticizing the Obama campaign for releasing the “glitzy fundraising video” on the same day the unemployment rate went up. The exchange signaled that the president’s close ties with the fashion industry could become a liability.

Whether or not Wintour’s power has affected designer turnout, it’s clear the fashion industry’s political clout is growing.

“The fact is that Obama now does fundraisers themed around fashion,” Collins said. “You’ve got to wonder why no one bothered doing it in the past.”

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Staff writer T.W. Farnam and researcher Madonna Lebling contributed to this report.