At an annual charity fund-raiser in October, Anna Wintour, the editor of Vogue, shared a table with the designer Michael Kors and Pete Buttigieg, then the mayor of South Bend, Ind., who wore one of his trademark navy suits.

The event was a benefit for God’s Love We Deliver, a nonprofit that began delivering meals to New Yorkers with AIDS in 1986 and has since expanded to serve other homebound people. On the second floor of Cipriani’s South Street location, guests bid for meals with the actor Neil Patrick Harris, watched the model Iman receive an award for her philanthropic efforts and heard a short speech from Mr. Buttigieg, who was also honored that evening. He said volunteers for the organization had offered sustenance “in substance and in soul.”

Sitting at a table near the stage was the theater producer Jordan Roth, who back in April held an event for Mr. Buttigieg’s presidential campaign at his home in the West Village, at up to $2,800 per head. Nearby was the board chairman of God’s Love, Terrence Meck, who had co-hosted an event for Mr. Buttigieg in Provincetown, Mass., just after the July 4 holiday. (Tickets for that ran upward of $1,000 per person.)

Neither of those events drew particular attention, partly because the campaign did not publicize them and partly because Mr. Buttigieg polled in the low single digits for most of the spring and summer, when he was less of a threat to rivals like Senators Bernie Sanders and Elizabeth Warren.

Even at the God’s Love benefit in the fall, the biggest news to come out of it was the enormous applause Mr. Buttigieg received from Blaine Trump, the ex-wife of President Trump’s brother Robert, who, in 2016, declined to endorse her former brother-in-law. (Although she didn’t walk around wearing an “I’m With Her” sticker either.)

But Mr. Buttigieg is now in a leading position in the Democratic primary, at or near the top of the polls in Iowa and New Hampshire and in fourth place nationwide. He is running to the right of Mr. Sanders’s populist rhetoric and Ms. Warren’s “billionaire tears mugs,” and offering a generational contrast to former Vice President Joseph R. Biden Jr.’s elder-statesman, Joe-from-Scranton appeal.

[Pete Buttigieg’s bet: As the Iran crisis grows, military experience matters more than ever.]

Mr. Buttigieg has talked in campaign videos and in interviews about how Democrats cannot just “polish off” a broken political system and expect to win.

So it is perhaps unsurprising that Mr. Buttigieg’s dinners and fund-raisers — complete with cozy pictures on Instagram of Mr. Buttigieg standing beside high-net-worth bundlers — have turned into grist for his critics.

Guests at a December fund-raiser for Mr. Buttigieg held at the New York home of Kevin Ryan, an internet entrepreneur behind Gilt Groupe and Business Insider, were greeted outside by protesters who banged pots and pans and called Mr. Buttigieg “Wall Street Pete.”

The police arrived when a protester got inside. By that point, Mr. Buttigieg had left for Ms. Wintour’s West Village townhouse, where a campaign dinner was being held. Tickets cost up to $2,800 each and the actress Sienna Miller was among the attendees.

Days later, Mr. Buttigieg appeared at a fund-raiser held inside a Napa Valley wine cave. Afterward, progressive activists reached deep into political crisis history to note that one of the hosts, Craig Hall, who is now the owner of Hall Wines in Rutherford, Calif., was a real estate developer involved in the savings and loan crisis in the 1980s. Mr. Hall went to Jim Wright, then speaker of the House, for help when he was facing bankruptcy — and the cascade of events led to a bailout for Mr. Hall, a congressional ethics investigation and, ultimately, Mr. Wright’s resignation as speaker.

Mr. Hall’s wife, Kathryn Walt Hall, co-hosted the Napa benefit. She was a prolific donor to President Bill Clinton and served as ambassador to Austria from 1997 to 2001.

The dinner for Mr. Buttigieg took place beneath a “raindrop chandelier with 1,500 Swarovski crystals,” The New York Times reported. To be fair, those sparklies can be found on $50 leotards. They’re barely more elite than Trump ties.

But that didn’t stop Mr. Buttigieg’s detractors from using them as a symbol of what’s wrong with him. To some, it seemed like a dishonest but effective way to make a substantive point.

Events like these are “not a good look,” said Rebecca Katz, a Democratic strategist who last year ran Cynthia Nixon’s primary campaign for governor of New York and who has not yet endorsed a presidential candidate. In an interview, she said that Mr. Buttigieg wants “to be in rooms with fancy people.”

Mr. Buttigieg’s supporters see it differently. They point out that Mr. Buttigieg has pledged to refuse money from federal lobbyists, corporate political action committees, foreign agents or executives from the fossil fuel industry (though he changed his position on lobbyist money with his campaign already underway). They also note that Mr. Ryan, who hosted the picketed New York event, previously held a fund-raiser for one of Ms. Warren’s Senate campaigns. (Ms. Warren, like Mr. Sanders, has sworn off high-dollar fund-raisers for this race.)

Prominent donors in Los Angeles argue that Mr. Buttigieg is also approaching celebrity fund-raising differently than Hillary Clinton did four years ago.

While her campaign publicized the appearances of Katy Perry and Lena Dunham at events, he’s kept a lid on similar associations.

The fund-raiser that Gwyneth Paltrow held on his behalf last May? The campaign declined to publicize it. Instead, Mr. Buttigieg spoke in front of cameras that evening during a $25 (and up) appearance at the Abbey — sort of a gay, West Hollywood equivalent of dining at Sylvia’s in Harlem with the Rev. Al Sharpton.

“He wasn’t doing a song and dance with Gwyneth on national television,” said Simon Halls, a prominent entertainment industry publicist who in July was scheduled to co-host a reception at the television producer Ryan Murphy’s home. (That event was canceled after a white police officer fatally shot a black man in South Bend; the reception has not been rescheduled.)

An offer by the designer Tom Ford to dress Mr. Buttigieg during the course of the campaign? Declined.

In July, Mr. Buttigieg appeared at the Provincetown fund-raiser Mr. Meck hosted with Bryan Rafanelli, an event planner whose clients have included the Clintons. Although tickets cost a minimum of $1,000, Mr. Meck said the event took place after a free, packed and publicized town hall event. As Mr. Meck told it, Mr. Buttigieg told him that he wanted to spend his time in Provincetown actually meeting people. Later in the summer, he hit the Hamptons to collect more money.

Yet Mr. Buttigieg’s rivals don’t seem to be cutting him much slack for the kitchen-sink approach.

At the December debate, during a lengthy and heated exchange about money in politics, Mr. Sanders joked that Mr. Buttigieg and Mr. Biden appeared to be in a race for who could collect the most donations from billionaires. Mr. Biden was winning, 44 to 39, Mr. Sanders said.

“We don’t keep track of that sort of thing,” said Chris Meagher, the national press secretary for the Buttigieg campaign, when asked whether this was true.

Mr. Meagher also didn’t answer a question about where Mr. Buttigieg camped out during his summer trip to the Hamptons. “I don’t know who he stayed with,” he said.

According to the latest data from the Center for Responsive Politics, Mr. Buttigieg’s campaign has received more money from the financial, insurance and real estate sector than any other candidate’s. On Wall Street, he has seemed to occupy the sweet spot on the political spectrum — perceived as a socially liberal and sensibly centrist former McKinsey & Company consultant who may increase taxes on the rich but most likely won’t break up big tech or the banks.

The Buttigieg campaign said Wednesday that it had received donations from more than 730,000 people over all, and that its donors contributed more than $24.7 million in the last three months of 2019. The size of an average donation was around $34, a statistic that campaigns like to use to show they are receiving money from grass-roots contributors, though Mr. Buttigieg’s number was considerably higher than recent averages reported by Mr. Sanders and Ms. Warren.

In late December, the Buttigieg campaign introduced a bizarre contest asking for the smallest contributions possible. Multiple entries were allowed and the person who donated the lowest “unique amount” would win a prize. Liberal activists and officials with rival campaigns said it was little more than a ploy to help lower the average donation amount in the days before fourth-quarter results were reported. (Other campaigns have also encouraged their supporters to donate in small increments.)

One of Mr. Buttigieg’s top fund-raisers is Orin Kramer, a hedge fund manager who in 2008 was described by the New York Observer as “king of the New York Obamasaurs.”

Another is Hamilton E. James, executive vice chairman of the Blackstone Group, a private equity fund headed by Stephen A. Schwarzman — an adviser to President Trump who in 2010 compared Obama-era tax hikes on corporations to Hitler’s 1939 invasion of Poland.

Both Mr. Kramer and Mr. James appeared on a list the campaign released in December of more than 100 individuals who had raised at least $25,000 for Mr. Buttigieg.

In New York, a key player in courting these people has been Zachary Allen, a former regional fund-raising director for the Democratic National Committee. In Los Angeles, the point person is Adia Smith Parker, who served in a similar capacity for Barack Obama during both of his presidential campaigns.

Ellen DeGeneres has given Mr. Buttigieg $2,800; Mr. Ford, double that.

It’s not just that Hollywood likes Mr. Buttigieg’s policies or personal story. It’s also that the entertainment industry is built off the need for attention; many who profess to like Ms. Warren’s policies also seem personally hurt by her seeming indifference to communing with them.

A substantial number of Mr. Buttigieg’s bundlers are gay men and lesbians, but the super-donors list shows that he has expanded beyond his early circle of wealthy L.G.B.T. supporters.

Mr. Meagher said the campaign had an “unprecedented” number of black men and women in high-level fund-raising positions (including Ms. Parker), but the bundlers list shows limited support coming from the network of significant African-American donors who provided Mr. Obama with essential support in the 2008 race.

“I do think he’s making efforts,” said Antjuan Seawright, a Democratic strategist in South Carolina who is black, referring to Mr. Buttigieg. “I’m just not sure it’s breaking through.”

Mr. Buttigieg has gotten some interest from Oprah Winfrey. Last April, she said she was reading his book, “Shortest Way Home,” but was having trouble pronouncing his last name. “I call him Buttabeep, Buttaboop,” she told The Hollywood Reporter.

She has not endorsed him. In fact, Ms. Winfrey said in September that her real first choice for president was Bob Iger, the telegenic chief executive of Disney. And Mr. Iger had flirted with running, only to decide that voters would see him as “just another rich guy who’s out of touch with America.”

Mr. Buttigieg can at least argue that he doesn’t have that problem. When his Democratic rivals took aim at him in the last debate over his glitzy fund-raisers, he quickly fired back, “I am literally the only person on this stage who is not a millionaire or a billionaire.”