The event, scheduled for August, is expected to bring more than 40,000 people from all over the country to Jacksonville, and while the rules may apply to them, it's likely Trump will exempt himself.
"I talked to the president before coming out here," McEnany said. "It's his choice to wear a mask. It's the personal choice of any individual as to whether to wear a mask or not. He encourages people to make whatever decision is best for their safety, but he did say to me he has no problem with masks, and to do whatever your local jurisdiction requests of you."
Her rationale comes on the heels of a growing number of health officials urging the public to wear masks as cases rise alarmingly across the southern United States.
At the first public task force briefing in two months last Friday, Vice President Mike Pence spent much of the time applauding the Trump administration's efforts and emphasizing how much worse the pandemic could have been without their response.
Coronavirus response coordinator Dr. Deborah Birx, meanwhile, stressed the importance of wearing a mask.
When asked by ABC News Correspondent Kyra Phillips why Trump's campaign continues to hold rallies without mask or social distancing requirement, despite public health advice, Pence cited the Constitution.
"The freedom of speech and the right to peacefully assemble is enshrined in the Constitution," Pence said. "President Trump and I believe that taking proper steps as we created screening at recent events, and giving people the very best counsel that we have. We still want to give people the freedom to participate in the political process."
Pressed about how masks -- or how the decision not to wear one -- has become a political statement, Pence would only say he encouraged Americans to follow state and local leaders.
For many people, that wasn't enough.
Rep. Liz Cheney, R-Wyo., House Republican Conference Chair and daughter of former Vice President Dick Cheney tweeted a photo of her masked father following the task force briefing accompanied by the hashtag "RealMenWearMasks."
House Speaker Nancy Pelosi also shared the sentiment to ABC News Chief Anchor George Stephanopoulos on "This Week" Sunday and voiced her support for a federal mask mandate.
"It's definitely long overdue for that," she said. "My understanding is that the Centers for Disease Control has recommended the use of masks but not required it, because they don't want to offend the president."
"Real men wear masks," she added. "It's not about protecting yourself, it's about protecting others."
By Sunday afternoon, Pence has changed his tune -- somewhat.
In a trip to the hotspot state of Texas, Pence and his team all arrived wearing masks, as did Texas Gov. Greg Abbott, a Republican, and his team, to greet Pence on the tarmac.
In a later press conference, Pence was more direct in echoing the advice of the health professionals seated beside him: "Wearing a mask is just a good idea."
Birx then stressed the importance of "100% compliance" with mask orders in several counties as hospitalization rates increase particularly among younger adults with underlying health conditions.
Notably, hours before Pence gave advice alongside Birx, he spoke at a mega-church in Dallas with over 2,000 congregants and a 100-person choir -- standing close and none wearing masks -- though the Centers for Disease Control an Prevention has warned churches can be "super spreader" sites, for one, because of singing.
Despite the ramped up warnings, Trump has signaled for months that he doesn't view masks as presidential and has resisted any pressure to be photographed in one in public.
"I just don't want to wear one myself. It's a recommendation. I am feeling good," Trump said at an April 3 coronavirus task force briefing. "I just don't want to be doing -- I don't know, somehow sitting in the Oval Office behind that beautiful Resolute Desk, the great Resolute Desk, I think wearing a face mask as I greet presidents, prime ministers, dictators, kings, queens. I don't know, somehow, I don't see it for myself."
Even as Trump's travels to more states where the coronavirus was spreading, and more Republicans like Senate Majority Leader Mitch McConnell say people "ought to" wear them and Sen. Marco Rubio, R-Fla., said, "Everyone should just wear a damn mask," Trump has resisted the pressure.
Although the White House says the president respects state and local mask mandates, Trump, himself, seems to be the exception to those rules.
At a Fox News "town hall" in Wisconsin last week, for instance, all participants were required to wear masks to enter at the event -- except for a socially-distant Trump and Sean Hannity.
But Jacksonville Sheriff Mike Williams said Monday that without a mask, someone may not be allowed into a business or venue. This includes the Vystar Veterans Memorial Arena in Downtown Jacksonville where the RNC is scheduled for August.
"We will continue to work on these plans as we get closer [to the RNC]," he said.
It seems unlikely come August that the Republican National Committee will force their nominee to wear a mask in the mega-indoor arena.
It seems more likely it's a "personal choice" the president will do the same as he's done so far.
ABC News' Elizabeth Thomas and Ben Gittleson contributed to this report.