The gathering is a gamble for the highly scripted Xi, who risks an unravelling of his carefully constructed image.
The first face-to-face meeting between Xi and Donald Trump at the US president's Mar-a-Lago resort in Florida will be a key test of whether the two leaders can overcome their vast differences and develop a personal bond.
The gathering is a gamble for the highly scripted Xi, who risks an unravelling of his carefully constructed image in the face of Trump's notorious unpredictability as they discuss contentious issues ranging from North Korea to trade.
The 63-year-old, who took power in 2012 and was granted the vaunted title of Communist Party "core" in October, is widely considered China's most powerful leader in a generation.
Known best for leading an anti-corruption campaign that has taken down some of the party's most eminent officials, Xi's unyielding approach to governance has invited comparisons to Mao Zedong -- and pointed to possible collisions with Trump.
Their contrasting styles -- reserved versus blunt, rehearsed versus spontaneous, controlled versus turbulent -- could see the pair clash, Hu Xingdou, a Chinese economics professor and expert on corruption, told AFP.
Both men have strong characters, Hu said.
Xi is likely to be more "stable" while political novice Trump could prove to be "reckless" on issues such as China's trade surplus with the US -- a constant source of irritation in Washington and an issue that Trump tweeted will make the talks "difficult".
Beyond their differing personalities, however, there may be more that unites the two leaders than separates them -- which could be crucial in striking a personal connection and finding some common ground.
"Both Xi and Trump are charismatic and have the traits of a strongman who is not afraid to take risks," China political analyst Willy Lam told AFP.
Chinese politics expert Cheng Li highlighted their underreported similarities -- bold nationalism paired with a tendency to sideline bureaucracy and prioritise domestic affairs.
Where Trump has said he will "make America great again", Xi has called for the "great rejuvenation of the Chinese nation", Cheng said in a blog post for the Brookings Institute.
And like millionaire's son Trump, Xi was born into privilege.
As the child of a respected Communist Party elder, Xi is part of the "princeling" generation -- the offspring of highly revered figures who played key roles in the revolution that brought the party to power in 1949.
Xi, typically seen on state television with a deadpan expression, has worked to combat the associations of his pedigree by highlighting his experience as one of China's "sent-down youth" during the Cultural Revolution, when millions of young urban dwellers were sent to live in poor rural areas.
His story is faithfully chronicled by a state-controlled media as he oversees a tightening of press restrictions, a crackdown on human rights defenders and a highly publicised campaign against corrupt officials.
Xi may find Trump to be a sympathetic ear -- the US president was elected on a promise of ridding Washington of out-of-touch "establishment" politicians.
He also seeks to control his political message at home, accusing media outlets of peddling "fake news" when he believes his administration is being unfavourably portrayed.
Trump has set a sumptuous stage for the meeting at his Mediterranean-style compound, chosen because "it's a place where he feels comfortable and at home" according to a senior White House official.
But Xi, who once shed his suit jacket and tie during a stroll with the equally composed former US president Barack Obama, is unlikely to feel so relaxed during the talks at Mar-a-Lago.
The Chinese leader, whose decision-making is clothed in utmost secrecy, will be at great pains to avoid the very public nature of Japanese Prime Minister Shinzo Abe's February visit to the resort.
That summit coincided with news of a North Korean missile launch, compelling Abe and Trump to set up an impromptu situation room in plain view of gawking onlookers -- a scenario Xi would want to avoid.
"If there are embarrassing moments (during the summit) and both sides actually have a big quarrel over North Korea, that is a risk for Xi because he cannot afford to lose face while China aspires to be the new centre of gravity for the world order," Lam said.
As the leader who headed a drive to stop Communist Party members from playing a game condemned by Mao as "a sport for millionaires," Xi will also be skipping the resort's signature offering.
"I think it's safe to say there's not going to be any golf," the White House official told reporters Wednesday.