Chris Minns will be the first NSW premier to brave the cold alongside top business leaders when he takes part in the annual Vinnies CEO winter sleepout.
Aiming to raise more than $10 million nation-wide to fund St Vincent de Paul homelessness services, the event is also a chance for the public and private sector to collaborate on solutions.
"It's an opportunity just for a brief period to experience what life is like if you are homeless and sleeping rough," Mr Minns said.
"And that small bit of empathy is so important for a broader understanding that we live in a community, that we live in a society and it's everyone's obligation to do everything we can to reduce the amount of homelessness and housing pressure."
Mr Minns kicked off the fundraising ahead of the June 22 event, announcing a $50,000 donation from the Premier's Discretionary Fund.
The premier will be joined by top executives from Lendlease, KPMG and other major firms that have the potential to make a difference in the housing sector.
Advocates are urging state governments to dig deep and build more social and affordable housing to address the root cause of the worsening homelessness crisis.
The City of Sydney council found almost 300 people were sleeping rough in the inner city in February, a 23 per cent increase on the previous year.
St Vincent de Paul Society NSW chief executive Yolanda Saiz said with rising cost-of-living and housing pressures many were seeking help for the first time.
"Rough-sleeping is actually only six per cent of the total homeless population," she said.
"It's really about insecure housing - people sleeping in their cars, people sleeping in tents, boarding houses or overcrowded dwellings."
The charity is calling on the NSW government to deliver 5000 new social homes a year to help address a 10-year waitlist for long-term accommodation.
City of Sydney mayor Clover Moore said the pandemic showed with the right political will, governments could find the money, resources and urgency to address major challenges like insecure housing.
The mayor wants a minimum of 30 per cent social housing and 20 per cent affordable housing in the state government's proposed redevelopment of the inner-city Waterloo estate.
The public housing precinct is the country's largest, currently home to almost 2500 tenants, with more than 85 per cent of dwellings provided by the government.
However, fewer than three in every 10 units in the new development will be devoted to social housing, which Ms Moore calls a missed opportunity.
Incoming housing minister Rose Jackson told AAP the government would review the redevelopment with an eye to increasing its percentage of social and affordable housing.
