A legacy of luxury
In the heart of Chicago stands a beacon of style that has fashionably dressed generations of gentlemen. Syd Jerome, now in its 66th year, is more than just a high-end haberdashery. It is a Chicagoland institution.

Scott Shapiro, Syd Jerome owner and president, says the essence of this iconic men’s retailer is elite customer service.

“Our clientele is probably, as I like to refer to it, your run-of-the-mill millionaires and billionaires. But that aside, we cater to everybody. We’re a multi-generational store, helping with all your clothing needs,” Scott explained.

The business was launched by Scott’s father in 1958 on Clark Street in The Loop. The store has moved five times during its existence but always within a few blocks.

“My father started in the business because frankly he had no choice,” Scott stated. “His father was a tailor. His uncles were merchants, all in the men’s clothing business.”

A family affair
Interestingly, Syd Jerome was not the name of Scott’s father.

“The name comes from my father, who was Syd, but he spelled his name S-I-D, and a gentleman named Jerry Frishman (who also worked in high-end men’s clothing), is where the Jerome came from,” Scott explained. “They decided to change the Sid to S-Y-D, which sounded a little more cosmopolitan, and used Jerome as the second name, because it sort of flowed.”

For Scott Shapiro, Syd Jerome quickly became his path in life.

“From a very young age, my brothers and myself were sort of committed to coming to the store,” Scott shared. “Not that we had much of a choice. Every vacation, every weekend, every holiday that we had a day off from school was spent in the store.

“I got a chance to see my father interacting with some of the notables of Chicago,” Scott said. “Some of the brightest minds in the city of Chicago, and some throughout the country and the world, were coming to my father to ask for his opinion about how they should dress. So, I said, ‘You know, I could do that.’”

In 2018, Sid Shapiro passed away. Although he never not to see the current store, the fingerprints of his legacy are pervasive. Everywhere you look, there are nods to Sid Shapiro’s favorites in men’s fashion from the blue pinstripe wallpaper in the dressing rooms to the blue flannel accents, a nod to Sid’s love for blue flannel 3- piece suits.

Today, Scott carries on his father’s legacy, maintaining all of the businesses’ high-profile relationships with athletes, politicians, and corporate CEOs while ensuring the store welcomes everyone who walks through its doors.

“The store itself sometimes could be a little intimidating, because of the merchandise that we represent,” Scott acknowledged. “But it comes as a surprise to most people who come in the store how approachable the store is. We have the ability to fit almost everybody’s needs at almost any price point, although they don’t think so at the time they walk into the store.”

The business
Syd Jerome has long been at the forefront of men’s fashion in Chicago balancing tradition with trends.

“Our original mission was to bring the best of European fashion to Chicago, but that’s evolved over time to include brands in North America,” Scott explained. “Our stalwart brands are still Canali, Isaia, Brioni. There are a couple brands from Canada – Samuelson, Jeff Victor – which cater to a different clientele. We try to be more than one dimension in what we do.”

Scott credits his robust tailoring team as one of the greatest strengths of Syd Jerome. “We’ve still got eight tailors on the payroll. Most stores have one, if at all. Some have part-time (tailoring). Some send it out. So, we’re committed to servicing the customer. Our foundation is all in customer service.”

Fashion emergencies. Check. Last-minute requests. Double check.

“It’s not unusual for somebody to come in the day of their wedding and need a tuxedo within hours because they found that their tuxedo didn’t fit,” Scott stated. “Problem-solving is probably one of our biggest virtues.”

Adapting to a changing landscape
The retail landscape in downtown Chicago has experienced significant changes since the pandemic, and Syd Jerome has had to adapt to stay in business.

“Retail in downtown Chicago has changed dramatically,” Scott said. “At one point in time, there was a men’s clothing store at every street and every corner, sometimes multiple. Now if you walk around, we’re it,” he added.

“Retail in The Loop has gotten very depressing since COVID,” stated Scott. “The people who used to come down, come down with less frequency. The people who live in the suburbs are afraid to come down.

“Everybody is going to a hybrid work schedule. That has had a major impact, because now with the flex schedule and fewer people in the office, people don’t feel like they have to dress for work, which was a big driver in our business.

“COVID pretty much changed the spectrum of the way people dress, how they think, when they come to the office. And we’ve had to change.”

Scott says Syd Jerome has evolved at a time when he says the economy in Chicago’s Loop has devolved. The days are long gone for Syd Jerome being a daily drop-in destination for attorneys on-the-go or corporate executives needing a new tie for an evening event.

“The shopping experience downtown has changed significantly,” explained Scott. “We no longer have a lot of off-the-street traffic. You don’t see as many people walking by the windows as we used to.

“Now the business has become more event-driven, more necessity-driven. People come to us for specific things as opposed to incidentals.”

Shapiro says that shift in consumer behavior has transformed his professional role beyond that of a store owner.

“I almost act as an ambassador of the city every day,” Scott stated, “Because almost on a weekly basis, somebody from the suburbs calls me and says, ‘Is it still safe to come downtown?’ I have to assure them that it’s safe to come to the store, and it’s safe to shop.”

What people should know
Syd Jerome, as a longstanding retail titan in The Loop, now stands tall as a veteran voice in Chicago’s rich merchant history.

“I want the people of Illinois to remember how vibrant the city was. And it’s not to say that Chicago isn’t a vibrant city, but The Loop was the crown jewel of the city,” Scott reminisced. “We’re a block away from City Hall. We’re two blocks away from the federal court. We’re three blocks away from Grant Park and the Bean. You know, this is an important area of the City of Chicago, and it was an economic driver of the city.”

Despite these challenges, Syd Jerome is arguably still the crown jewel of the high-end men’s fashion scene in Chicago.

“I want the people of Illinois to know that we’re still here,” Scott stated with emphasis to underscore that he had no plans to ever leave The Loop.

“You asked me why I’m still here. It’s because of our customer,” Scott said. “Our customer is still the foundation of The Loop. We’ve been committed to them as they have been committed to us. We feel we need to be here for them. And we couldn’t achieve the same level of customer service and relationship if we were elsewhere.”

“We’ve endured because we’ve had the great support of our customers and our friends, and we continue to provide the same level of relationship, customer service, expertise, and selection,” Scott said with a prideful grin. “We’ve never deviated from our mission, and we’re proud of that. We always think tomorrow is going to be better. And you know what? Tomorrow has been better.”