Inside a Chicago Shop that Still Makes Suits Completely by Hand

Meet the craftspeople at Richard Bennett Custom Tailors & Shirtmakers who measure, cut, and stitch each garment the old-fashioned way.

In a big, bright window that looks out on Financial Place, the six mostly gray-haired craftspeople snipping and sewing resemble an anthropological exhibit.

“At most clothing shops, they keep the tailors in the basement below a drainage pipe,” jokes Albert Karoll, the appropriately well-dressed owner of Richard Bennett Custom Tailors & Shirtmakers. But here, in the heart of the Loop, these proud relics—a veritable dream team of tailoring talent from Europe and the Middle East—are placed front and center so passersby can appreciate the precision of their handiwork.

One of the city’s few remaining true custom shops—with a lineage that goes back to 1929—Richard Bennett caters to well-heeled professional types willing to drop two grand or more for a bespoke suit. In today’s hypercasual era, where “formal sweatpants” is an actual fashion term, a store that constructs fine garments completely by hand should not exist.

“I realize that I am swimming upstream,” says Karoll, 53, who reminds me of a sturdier John Malkovich and is wearing suspenders featuring a cappuccino cup pattern. “I recognize that a thousand percent. And I don’t care. I’m not going to change.” The dedication to traditional tailoring is in his blood: His grandfather Herb, who owned a local chain called Karoll’s Red Hanger for more than five decades, lured him into the family business after Karoll had toiled for a few penniless years in his early 20s as a freelance writer.

“My grandfather sat me down,” he recalls, “and said, ‘Writing is a nice hobby, but it’s time you found a real job.’ ”

Ouch. Maybe that explains why the closest I’ve come to custom clothing was back in high school, when my mother took me to buy a sports coat at the specialty shop Wallaby Station, which featured a cuddly marsupial mascot and sold “apparel for the shorter man.” A stocky 5-foot-7, I’ve never really found clothes that fit. Suits are especially challenging: Too large, and I look like the guy who borrowed his dad’s clothes for the big meeting. Too small, and I resemble a stuffed sausage. Many of Richard Bennett’s customers came to him because they share my same problem, if not my modest bank account.

On a brisk Friday morning, I pop into the handsome, oak-countered boutique to be measured for my own custom duds. But I also want to check out this old-school trade in action.

Near the work area, I pass framed photos of local celebrities and sports figures who have turned to Karoll—among them, former Bear Devin Hester, ABC-7’s Mark Giangreco, and Wilco’s Jeff Tweedy. Karoll once performed an on-the-spot recutting job on 10 pairs of ill-fitting trousers for Tiger Woods that were part of his required Ryder Cup gear. “He was literally busting out,” Karoll recalls. “His quads are enormous.”

One whole wall at Richard Bennett is dedicated to fabric, stacked with more than $100,000 worth of fine woolens and silks from mills in England and Italy. Inside the work area, I notice a slightly metallic scent from the ancient steam irons used to gently shape raw sections of fabric. Here, I meet Ioan Sandru, the shop’s 60-year-old Romanian-born lead tailor, his measuring tape draped over his shoulders like a boa constrictor. He uses a massive pair of scissors to slice through two plies of dark gray cloth. Harrumph, harrumph, harrumph.

In Romania, Sandru worked at a factory that churned out 400 suit coats every day. At Richard Bennett, he oversees the completion of just three suits a week. He starts by translating a customer’s 40-plus measurements to paper and cutting the pattern pieces out like a jigsaw puzzle. He places these on the fabric, on which he chalks an outline that looks like something from a swanky crime scene, then cuts them out by hand. Familiar shapes reveal themselves: There’s a lapel. And there’s a pant leg. Once cut, the garment makes its way around the room to the other pros. Like Cornelia, a kind-looking 60-something Romanian woman who does much of the fine needlework. Eleanor, who is around the same age and from Lebanon, makes the pockets.

Today, a Slovak woman named Sylvia sews buttonholes by hand. “It is very difficult to do properly. The stitches have to be very uniform,” says Karoll, who explains that every hole takes about five minutes, whereas “on a machine it takes five seconds.” But hand-stitching brings pliancy, resulting in a hole that provides a bit of give when buttoned up—a touch of elegance.

The days when Don Draper types would bust out their fineries at the office are over, but Karoll thinks that sartorial shift has helped his business. Instead of a closetful of suits, a guy typically has only one or two. “And he wants them to be a knockout,” he says. “If someone is into authenticity, then we’re his place.”

But can it be a place for me?

It’s measuring time, and I decide that splurging on a pair of dress pants is the best way for me to delve into the world of custom duds. Karoll and Sandru begin with a fashion interrogation: What sort of occasions do I typically attend? What other wardrobe pieces do I own? Do I wear a belt? Then comes the fabric choice. Karoll shows me a dark gray Australian merino wool. It sounds expensive. I’ll take it.

The men scrutinize my physique like I’m a blue-ribbon hog at the state fair. Sandru grabs what looks like a large wooden T-square ruler (or a medieval torture device), which I’m told to basically straddle. This will determine my rise, which is the distance from my junk to the top of my waistband. At one point, he holds me firmly by the hips like we’re dance partners. I half expect him to ask me to cough.

I discover I am slightly bowlegged and my waist size is two inches bigger than I’ve been telling myself for the past decade. Despite the poking and prodding, I enjoy the process. I feel like I’m being pampered. I feel like a real adult man.

When I return to the shop for my fitting, the pants hug me in all the right areas. It’s like they were made especially for me, which, of course, they were.

Will they give me a confidence boost? I’m not sure. But I’m thankful to have scored some sweet custom trousers made by a master before the robot overlords take over.

This article appears in the February 2017 issue of Chicago magazine