The event-specific symbol features what appears to be a high-five between a hand representing the US president and one representing the North Korean dictator known for executing his political enemies and exiling large swaths of his nation to prison camps, where they face starvation and torture.
Kim was heard telling Trump through a translator: "I think the entire world is watching this moment".
It was a day of pleasantries, but little public substance. "We're going to have a great discussion, I think, a tremendous success, this will be tremendously successful".
The leaders approached each other on a red carpet from separate outdoor hallways at the airy and luxurious Capella Hotel on Singapore's Sentosa Island.
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After briefly moving away from the media glare, Mr Kim and Mr Trump reappeared, walking together along a balcony and posing for pictures.
President Moon Jae-in and his cabinet watched the start of the summit before their morning meeting at Cheong Wa Dae ("Blue House"), the South Korean news agency Yonhap reported.
Experts believe the North is close to being able to target the entire US mainland with its nuclear-armed missiles, and while there's deep skepticism that Kim will quickly give up those hard-won nukes, there's also some hope that diplomacy can replace the animosity between the USA and the North. "We will be fine!"
The thaw, however temporary, is a far cry from past year, when Trump threatened North Korea with "fire and fury" and mocked Kim as "Little Rocket Man", and Kim slammed Trump as the "mentally deranged United States dotard".
Kim is due to leave on Tuesday afternoon, a source has said.
While there has been a wave of bipartisan voices looking to support the president's efforts to avert war in the Korean peninsula, there have also been concerns in foreign policy circles that the meeting will elevate Kim's status as a brutal dictator overseeing a regime complicit in horrendous human-rights abuses.
Pompeo declined to comment on a question about the approximately 28,500 US servicemembers based in South Korea.
In the meeting room, the leaders sat side-by-side. This week, the president said he looked forward to getting to know his new negotiating partner.
In any case, the Trump administration has no choice. It's a price they are willing to pay for peace.
Trump and Kim may discuss the prospects for a peace treaty involving South Korea.
At one point, Trump suggested to reporters the talks could extend to a second or even a third day if they were going well. He bounced to the Singapore summit after a tempestuous G-7 summit where the USA was isolated from its key European partners as never before and Trump even derided his Canadian host, a paragon of liberal democracy, as "dishonest" and "weak".
Described by his critics as a mini-Stalin, Kim has been on something of a charm offensive in Singapore since arriving Sunday.
Trump advisers cast his actions as a show of strength before the Kim meeting.
With cameras of the world's press trained on them, Trump and Kim displayed an initial atmosphere of bonhomie. "He said: Can you do that".
On his stroll, Kim had been briefed on urban development plans. That could lead to misunderstandings, he said, if there are no witnesses to record what is said. "We will be tremendously successful", Trump said before their private session.
The US has offered North Korea "unique" security guarantees to persuade it to give up its nuclear arsenal, Secretary of State Mike Pompeo said on Monday, on the eve of a historic summit in Singapore. "Sanctions will remain until North Korea completely and verifiably eliminates its weapons of mass destruction programs".
It's important that participants not oversell progress in Singapore, analysts said. Past nuclear deals have crumbled over North Korea's reluctance to open its doors to outsiders.
"AP is troubled by the decision to curb media access at the Singapore summit", Easton said.