Every Sunday at 4pm, homeless people from the streets of Sydney gather under the bridge at Cathedral Street in Woolloomooloo, and wait for Penny Kehoe.
The 43-year-old former teacher and youth worker lays out piles of items on tables as upwards of 100 people await a pair of new shoes and fresh clothes.
With her trademark red cap and bubbly personality, she’s built a community among one of the most vulnerable groups in the city.
Including making them: “The best dressed men in Woolloomooloo!”
Kehoe founded the service, Homeless Not Nameless in 2017 after volunteering for Street Buffet. There, she realised the need for new clothing for homeless people.
I had a cupboard full of towels at home, so I brought some the next week and nearly witnessed a fight over them.
“One night, a homeless man asked if I had a towel,” she says. “I didn’t, but I asked if towels were something they needed.
“I had a cupboard full of towels at home, so I brought some the next week and nearly witnessed a fight over them. Then someone asked for dry socks, which I had plenty of.
“That’s when I realised the huge demand for basics like clothing and hygiene items. So I started collecting more, and every Sunday, we’d go down to distribute them.”
Obtaining clean and weather-appropriate clothing can be difficult for many homeless people.
But Kehoe bridged this gap, collecting lost property from gyms, pools, and major events. Many of these items are often unworn and brand new, and would’ve otherwise been wasted.

Penny Kehoe sorts through items as rough sleepers search for new clothes. Photo: Roman de Vallance.
“At City2Surf, there were 90,000 runners and nearly that many jackets! The collected gear usually lasts us until the next winter,” she says.
“I bring everything home, sort it, wash it and dry it. I organise and pack the clothing into bags and store it until next Sunday.”
She says socks are donated from Grip Star, underwear from Sparx/Vanta, blankets from United Airlines and toiletries from Qantas cabin crew.
The overwhelming majority of people Kehoe caters for are men, but no one is ever turned away.
For homeless people, clothing, toiletries, and sleeping gear is more than just simply that.
“No one should look homeless. Clothes give them dignity. They can walk into a shop or see their families and feel presentable. They want to look clean, put together, not like they just slept on concrete,” Kehoe says.
Along with Sunday’s clothing spread for the rough sleepers of Woolloomooloo, Kehoe provides ‘Wellness Bags’ to correctional services for inmates who are at risk of homelessness on release.
These bags are delivered to the jails across NSW, and are distributed among inmates by prison employees on release.
To help prisoners transition from jail to the streets, each bag includes a change of clothes, toiletries, and rough sleeping gear.
Kehoe’s goal with Homeless Not Nameless is to pay rough sleepers to pack the ‘Wellness Bags’.
“I’d love to employ the unemployed because these guys need work. They need a job, a reason to get up, a focus and most of them deserve that,” Kehoe says.
I was briefly taken into custody and then I became homeless.
For homeless men such as Josh*, Kehoe’s help benefitted his transition from prison to the streets.