"Slowly we are starting to see people we haven't seen in the last two years and we feel confident enough that we're going to see more activity by the end of the year," Shapiro said.
The business started by Shapiro's father some 63 years ago has survived and is known for outfitting everyone from politicians to famous athletes, and even the pope, who received a gift purchased from Syd Jerome.
The protective window boards at the designer men's clothing store came down early this weekend.
They were originally put in place some 14-months ago following the unrest sparked by the murder of George Floyd.
"Some of the firms have come back already. Courts are starting to open up [and] we're starting to see men walk around in suits instead of sweats," Shapiro said.
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There were also several grab-and-goes, including one where Shapiro was hurt.
"It was after that August 10 event that we decided to board up and it wasn't until this morning that we took the boards down, just because we didn't feel secure enough," Shapiro said.
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Although the store located at Clark and Madison streets has remained open to customers in some form during most of the pandemic, it officially re-opened Saturday as foot traffic in Chicago's Loop continues to climb.
According to the Chicago Loop Alliance, which tracks pedestrian activity and hotel and office occupancy, Loop activity last month was more than 50% of pre-pandemic levels and even higher over Labor Day weekend.
The alliance added that other establishments, including Petterino's Restaurant, reopened earlier this month as Chicago's theatre scene resumed, possibly bring more people and tourists to the Loop.
All good news, Shapiro said, who is banking on a Loop comeback.
"I believe that the Loop isn't dead, it's just sleeping," he said.