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If you walk down Jackson Boulevard in the Loop – eyes off the electronics for a moment – you might spot a little Chicago history working away behind a huge picture window. A group of tailors, hand stitching, ironing, and cutting custom clothes as the company has since the 20’s.

Today Albert Karoll is the man behind Richard Bennett Custom Tailors.

“My grandfather, Herb Karoll, was the founder of our retail entity known as Karoll’s Red Hanger Shops Ready-Made,” Albert said.

In the 1920’s Herb Karoll began the family business, outfitting some of the city’s most well-known for decades out of a store at State and Washington. Having no interest in it as a child, Albert didn’t get involved until the late 80’s when the family business went under.

“I had started selling custom-made clothing as a direct salesman. I had a tape measure, I had a car, and I had a phone, and I would go out and see my clients by appointment, measuring them and outsourcing the work to other tailor shops,” Albert said.

Through the years the company acquired Richard Bennett as well as D. Debartolo, a tailoring company opened by an Italian immigrant in the 20’, whose business thrived on the hands of European tailors painstakingly crafting each garment as they do today.

“They are the unique feature of what we do as opposed to everybody else,” Albert said. “It’s about seven or eight histories and legacies altogether.”

Today Albert celebrates more than eight decades focused on the old world craft in an ever-changing society built on technology and speed.

“It’s hard to do in this economy; people are sensitive to price, there are lots of different ways to buy clothing these days including the Internet, but we feel we’re a little like the marines: we’re looking for a few good men – and women,” Albert said.

Women are a fast-growing segment of the business. What used to be 5% of work back in the day now accounts for close to 20%. Growth happily accepted as society moves from regular suits and dresses to more casual attire at home and work.

“Let’s face it: a pair of jeans or a knit polo shirt can be more comfortable but it’s only more comfortable than dress clothes if your dress clothes don’t fit you properly,” Albert said.

Fit, personal interaction, and listening to his customers is what Albert says has kept them going for so many years. His styles are classic: shirts, suits, ties, hats. The look of the Golden Age of men’s clothing. An updated Rat Pack style, always in fashion.

“Those guys looked cool right? The Rat Pack, everyone wants that. I don’t know if 30 years from now anybody’s going to look back and say Justin Bieber was the cool guy,” Albert said.

It isn’t fast. It isn’t cheap. It is an investment, Albert says. One to last decades, as the craft has. And as the world moves full speed ahead he’s confident his timeless creations will as well.

“The more the world goes digital, the more the world goes Internet, the more the world goes discount, the more the world goes mass replication, I’m just going the other direction. I’m going to find my audience staying true to what we do.”

Richard Bennett Custom Tailors
175 West Jackson, Chicago, IL 60604
(312) 913-1100