The holiday handout, which also included treats and festive music, was all an effort to help the men elevate their futures.
The group felt the holiday spirit as they received the gift of new clothing just in time for Christmas.
It took only a few minutes for Marquate Swift to decide on his perfect look.
"I've been going through a lot of situation lately. I'm trying to get back on track," Swift said.
The 47-year-old Chicago man is one of dozens of men who received brand new men's clothing during the first-ever Christmas at the Mission event at the Pacific Garden Mission.
It's a South Loop shelter that roughly 400 unhoused or housing insecure men call home.
"The fact that people walk through our doors and put their arms around them is a blessing," Pacific Garden Mission President Phil Kwiatkowski said.
The Chicago not for profit I Am A Gentlemen, which is known for its male mentoring programs, hosted the event along with its sponsors.
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"We wanted to make sure we provided them the tools and resources to not only feel good, but look good as well," said Jermaine Anderson, executive director of I Am A Gentlemen.
The holiday initiative coincided with a rare evening address from the White House by President Donald Trump, during which he bragged about a good economy.
"One year ago, our country was dead. We were absolutely dead. Our country was ready to fail, totally fail. Now we're the hottest country anywhere in the world," Trump said.
Terry Crandall says that's not how it is in his world.
He's currently working loading trucks, but hopes the new clothes will bring him some confidence for a new job.
"I was probably saying a nice dress shirt so I can go to interviews and try to find a better job," Crandall said.
According to U.S. Census data analyzed by the ABC7 Chicago data team, in Chicago, the unemployment rate is 7.3%, but the Black unemployment rate is nearly twice as high, at 14.2%.
Despite the reality, Calvin Dilworth remains optimistic.
"This actually motivates me because I'm in the shelter; I don't have my own place. And so that in itself is motivating to move up," Dilworth said.
The group's outreach doesn't stop there. On Christmas Eve, they're planning a holiday dinner and Christmas gift giveaway for several hundred families.