Freeman steps into shoemaking niche

MIDDLEBURY — “Just speak up if we can help you,” Dan Freeman called to the customers who’d ambled into the Middlebury shoemaker’s shop.
Just as quickly as he’d looked up, he was back to work. Behind his worktable, Freeman’s hands were in constant motion — stretching the leather in one shoe, and boxing up another pair to ship off to a customer. He pulled lasts, the foot-shaped models used for designing shoes, from the crowded shelves around his workbench.
Welcome to Dan Freeman’s Leatherworks, one of fewer than a dozen shops nationwide devoted to custom shoe- and boot-making.
Zebra finches chirped in a cage dangling above one of Freeman’s display cases, keeping with a mysterious tradition that dates back thousands of years. If you can believe the Greek historian Plutarch, Freeman said, ancient Greek and Roman shoemakers kept caged birds, and leatherworkers in Europe during the Middle Ages did, too.
“I think it’s because they didn’t have CD players,” Freeman joked.
Freeman, 63, has plenty of diversions: He runs a retail portion of his shop to sell belts and wallets and purses, and the door opens and closes frequently during the summer months. But in the winters, he spends long, quiet days in the shop, stitching away on leather.
Watch Dan Freeman tell the story of how he began leather working in this this multimedia profile.
A native of North Carolina, Freeman came to leatherworking by happenstance. As a child, he said, he wasn’t any good at sports or academics, but he could work with his hands: He delighted in building model airplanes. Though he went to college for a few years, he never graduated, and he was eventually drafted into the military.
When his tour of duty was up, he came home to North Carolina. He was looking for work, and it just happened that a friend had started a prosperous business making sandals for the students at the University of North Carolina. Freeman went to work. Around that time, he met his future wife, Susan, while she was studying for her master’s degree at UNC.
She was a Vermonter, and when she graduated, the couple migrated north — and Dan Freeman brought his leatherworking tools along.
He and a few partners opened a leatherworking shop on Main Street in Middlebury, where Forth ’N’ Goal is today. They made all kinds of goods out of leather, including moccasins and “hippie sandals,” but Freeman wanted to learn how to make proper shoes. Learning was easier said than done.
“There are no schools, there are no books,” he said. “There’s no information at all about it.”
Then, in 1976, Freeman struck up a providential conversation with a Tulane University student living in Middlebury for the summer. He told the student about his interest in shoemaking, and the student, as luck had it, knew about an old shoemaker working in New Orleans.
Freeman wrote a letter to the man, but never got a response, so he boarded a Greyhound bus and rode night and day until he reached the Crescent City. At first the shoemaker, an old Jamaican man, told Freeman to go away — but when Freeman stuck around, and proved he was serious, the man struck a deal.
“Finally he said, ‘All right,’” Freeman recalled. “‘If you want, you can work for me as long as you want, and I’ll teach you everything I know, and I won’t charge you a penny.’… Some deal.”
So Freeman and his wife loaded everything they owned into a U-Haul truck and moved their fledgling family south without a job or a place to live. Susan supported the family teaching in New Orleans inner city schools while Dan studied in the old shoemaker’s shop.
“Needless to say, she hasn’t been in a shoe shop since,” Freeman said, “and I still owe her a bunch more pairs.”
Freeman has been in his Park Street shop, just off Middlebury’s Main Street, since 1986. “Lasts” line the walls — these are the forms Freeman creates for each of his customers, designed to mimic the exact shape of that person’s foot. No two are alike. The shoes on display range from tiny oxfords and simple sandals to tall, elegant equestrian boots and rugged hiking boots.
Freeman has had apprentices of his own come to learn the trade, just as he did in New Orleans. Most are interested in the satisfaction of making their own pair of shoes, or are looking for something new to try. Fewer — maybe 10 percent — are like Freeman.
“They just know that this is what they want to do. They don’t want to do anything else,” Freeman said. “They realize how hard it is, they realize how complicated it is, and they still want to do it.”
Apprentices aren’t the only ones who seek Freeman out: His customers do, too. He’s particular, though. On a recent afternoon, he sadly turned away a man with wide, size 18 feet looking for a pair of custom sandals. The man was visiting from out of town, and Freeman insists on several fittings for each pair of shoes he makes.
“I should just take peoples’ money, but I can’t,” he said ruefully after the man left the shop, but the shoemaker’s pride wins out over business savvy. Freeman is insistent that a pair of shoes fit perfectly, and if they don’t, he won’t make the customer pay. Some of his examples around the shop are examples of those not-quite-right near misses.
Some customers are persistent. A woman from Kentucky refused to take no for an answer when Freeman told her he only makes local shoes. She told him she’d fly up as often as need be to have her shoes fit, and she and her husband have been back three times since.
It’s the hiking boots and dress shoes he makes the most of, and almost always they’re crafted for a customer with unusually sized or shaped feet — like women whose feet range from size three to size 16. Most people lose interest when they realize just how much a custom-crafted pair of shoes costs, Freeman explained: A single pair can cost around $1,000, and the first is even more expensive because of the cost of creating a last and performing initial fittings.
They’re also hugely time-consuming to build. Freeman picked up a men’s dress shoe. Even after he’s created a last and a pattern, he said a shoe like that could take between 16 and 24 hours to craft. He’ll make a model shoe first, and tweak that to a customer’s fit, before moving on to the final product. Some customers ask that he hand-sew the seam connecting the shoe to the sole, and that adds even more time to the process.
Freeman gets most of his leather from Texas, and his soles come from a supplier in Ohio. He used to travel down to the “leather district” in Boston, but that part of the city has been gentrified and the leather dealers have disappeared. Finding these materials can be hard, because it’s a shrinking market, but there’s still a demand for it. You just have to know where to look, Freeman said.
The shoe repair trade, meanwhile, has died off horribly. Freeman guessed that at least once a day he has to tell someone that he can repair their $60 shoes — but it would cost the person $180 to do so.
“Almost no shoes are worth repairing now,” he said.
But Freeman isn’t worried about the shoemaking trade drying up anytime soon. Thirty years ago, when he was just getting into the business, people warned him that shoemaking was a dying business — but he’s still going strong, even though his jack-of-all-trades niche in the shoemaking world is a small one.
There are hundreds of orthopedic shoemakers in the country, he said, who design shoes specifically for patients with health concerns, deformities or amputations. Another 50 to 200 people make custom cowboy boots — a lucrative business that caters to everyone from businessmen to country music stars to rodeo riders. In fact, the man considered arguably the most famous cowboy bootmaker in the country today — Lee Miller, of Austin, Texas — is a Rutland native, and makes boots for the likes of Lyle Lovett and Willie Nelson.
Freeman is unique among cordwainers because he hasn’t specialized in any one kind of shoe. He guesses there are only about 10 people in the country who do what he does.
Choosing not to specialize in any one kind of shoe means he hasn’t perfected a model yet — but it keeps the work interesting. He hasn’t made ice skates or ski boots yet, because the equipment is just too specialized, but otherwise Freeman thinks he’s tried his hand at just about every kind of shoe he’s wanted to try. He likes the challenge of seeing if a shoe can live up to the image he has of it in his head, or if he can copy for a customer a particular design or aesthetic.
The most important thing, though, is fit.
“What I work for above all else is to see the client put on the shoe and smile … and say, ‘You’ve got it, Dan, this is great, these shoes fit.’ I’ll do anything for that,” Freeman said. “When you get somebody who is really hard to fit, and their feet do hurt just because shoes are not designed for them, and you can make a shoe that fits them, that’s the best thing to happen.”
He’s outlived some of his customers, and inherited others who will bring him their lasts after their own shoemaker dies. Early in his career, he made shoes for one woman until she was 94, and periodically would receive a letter in perfect script: “Dear Mr. Freeman, I require another pair of shoes.”
You get to know a customer well when you make their shoes, he said. He tapped the men’s dress shoe again.
“This is the 15th pair I’ve made for this customer, and they fit perfectly every time,” Freeman said. “But I’ve had a lot of practice to get it right … Every year more and more of the shoes fit the first time, and fewer and fewer don’t fit at all.”
Reporter Kathryn Flagg is at [email protected]

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