Chicago’s retail graveyard is crowded with menswear stores: Baskin, Mark Shale, Brittany Ltd., Bigsby & Kruthers among them.

But 60 years after Sidney Shapiro co-founded his clothing shop — at a time Eisenhower was in the White House, Sputnik was in space, and a young Elvis was still swiveling his hips — the Syd Jerome store at 2 N. LaSalle St. in the Loop is going strong.

He dressed lawyers, traders, doctors, politicians, athletes and musicians. Rapper Flo Rida once bought a suit at Syd Jerome to match the color of his Mercedes Maybach, according to Mr. Shapiro’s son Scott Shapiro. Others the elder Shapiro outfitted included both Mayors Daley, numerous Chicago Blackhawks, jazz piano great Ramsey Lewis and singer Stevie Wonder.

Dressed in double-breasted suits, pocket squares and a fedora when it was cold, Mr. Shapiro was his own dapper advertisement for the business until his death at 86 in August.

Sid Shapiro wearing a then-fashionable Nehru jacket in the late 1960s. | Provided photo

“As a person who served the public, he was the best I ever encountered,” said attorney James D. Montgomery, who marveled at how Mr. Shapiro directed his tailors to take in or add just a bit here or there to transform a suit into a perfectly elegant exoskeleton.

“The first thing I do is look at you, I can tell you what size you are,” the clothier once told WBBM-TV.

After Robert A. Clifford became a lawyer in 1976, Mr. Shapiro told him: “You have to have a sincere brown suit for closing arguments, so the jury believes you. And you have blue eyes, so you have to wear a blue-ish tie to pick up the color of your eyes.”

“Here I am 42 years later,” the personal injury lawyer said, “and, for closing arguments, I’ve always worn a brown suit.”

Sidney Shapiro (right) and his son Scott Shapiro posing with the Stanley Cup at Syd Jerome menswear, 2 N. LaSalle St. Mr. Shapiro outfitted many Blackhawks players. | Johnny Burbano Photography

Sidney Shapiro (right) and his son Scott Shapiro posing with the Stanley Cup at Syd Jerome, 2 N. LaSalle St. Mr. Shapiro outfitted many Blackhawks players. | Johnny Burbano Photography

Leo Melamed, chairman emeritus of the Chicago Mercantile Exchange Group, called Mr. Shapiro “a genius retailer.” Melamed’s office is lined with photos of him with a parade of presidents, prime ministers and Federal Reserve chairmen. “In every instance,” Melamed said, “I was wearing a Syd Jerome suit.”

When Melamed had a power meeting coming up, he said he would have a “call Sid” moment. “There were times absolutely when I needed a garment, either a suit or a jacket or a pair of pants, something happened, and I was leaving in the morning,” he said. “You’d give him less than 12 hours, and he outfitted you to perfection.”

Mr. Shapiro knew big-name designers Giorgio Armani, Michael Kors and Gianfranco Ferre. But he never forgot his job was to take care of his core Midwestern clientele, Melamed said. “Whether they were white, black, brown, it didn’t matter,” he said. “They were just his customers.”

When Janet Pioli was planning her wedding in 1996 in Grand Cayman, the hotel insisted she sign a $1 million insurance policy to cover any damages. Her husband-to-be Evan Karnes mentioned that while shopping at Syd Jerome.

“Evan said he called one of the people he dresses who happen to be affiliated with the hotel,” Pioli said, and then the resort’s catering chief told her: “Janet, I was told to do whatever you want.” The demand for the whopping insurance policy was dropped.

Mr. Shapiro’s parents, Sarah and Leo, a tailor, were Jewish Eastern European immigrants. When he was 11, he came home from school to find his mother had died of a stroke while cleaning their home for the Sabbath, his son Lee Shapiro said. Mr. Shapiro’s father died of emphysema when he was 16.

Lee Shapiro said his father grew up with cousins on the West Side and went to Bryant grade school and Marshall High School, where he was on the basketball team.

He said Mr. Shapiro started working as “a puller” on Maxwell Street when he was just 11, perfecting a patter — “Youlookinforasuit? Howmuchyouwannaspend?” — to draw customers to come in to stores.

Sidney and Muriel Shapiro, his wife of 65 years. | Johnny Burbano Photography

During the summer, he’d head to South Haven, Michigan, and work as a lifeguard. When a friend brought him home, he met Muriel “Cissie” Smason, who would become his wife of 65 years. They settled in Highland Park.

He became the top salesman at Smoky Joe’s men’s clothing store at 1233 S. Halsted, where clients could be outfitted monochromatically head to toe with matching shoes, socks, suit, shirt, tie, overcoat and hat.

In 1958, he opened Syd Jerome at 46 S. Clark with Jerry Frishman, a partner he later bought out, according to his family. They took the store’s name from their first names, with a small tweak because “ ‘Syd’ looked fancier on the letterhead,” Lee Shapiro said. The store relocated a few times before moving to 2 N. LaSalle St.

He is also survived by another son, Jeff Shapiro, and seven grandchildren. Services have been held.