BRIT EATON'S PATH INTO the vintage-denim business was as circuitous as the occupation itself. The son of an investment banker and a mother with an interest in archaeology, he was born in Princeton, New Jersey, in 1970 and raised in a home dating back to the 18th century. His mother, Landis, believes that Brit inherited "the looking-for-things genes" from her. During spring-cleaning season, she would strap him into a car seat and drive around to see what their neighbors had put out on the curb. "He never liked to wear anything but old stuff, and he was always an entrepreneur," she says. As a kid, he sold pumpkins and lemonade at a roadside stand, and when he got a little older he tried expanding his product line to include lead toy soldiers that he produced with a Bunsen burner and a hand-casting mold. He remembers taking some of his product to a local Kmart in an unsuccessful bid to broker a wholesale contract.

In 1988, Brit enrolled at Rollins College, in Winter Park, Florida. He spent his junior year in a semester-at-sea program that took him around the world, and the journey left him with him a deep wanderlust. After graduating, in 1992, he shipped an old Harley-Davidson to Rotterdam, Holland, thinking he'd tour Europe on two wheels. He rode the bike up to Norway, where he sold it for twice what he'd paid. Brit knew a solid business opportunity when he saw one, so he returned to the U.S. and escorted three more Harleys to Europe in 1993. He might have stayed in the motorcycle-import-export business if he hadn't gone to a party one night in Princeton, fallen into a window well, and broken a few ribs. "That made it pretty much impossible to kick-start old bikes," he says.

Over the next few years, he racked up an impressive roamer's résumé: He was thrown in jail in Greece; drove a cab in Madison, Wisconsin; created and sold T-shirts at Grateful Dead concerts; sold ice cream on nudist beaches in Holland; got caught up in a multilevel marketing scheme in Florida; and worked for a company that organized trekking expeditions for Americans traveling in Europe. In early 1997, he took a job working on a swordfish long-liner out of Puerto Rico. He was confined to his quarters for insubordination, but the trip had a positive outcome. A fishing captain from another boat mentioned to Brit that his mother worked for an import-export agent who had a 1,000-pound, compression-packed bale of used Levi's in a Florida warehouse. It reminded Brit of something he'd heard a few years before, when a Norwegian Harley-Davidson customer suggested he import vintage Levi's along with bikes.

Brit returned to Florida in April 1997 and bought the bale for $750, then took it to a home where he was staying in Fort Lauderdale. When he cut the bale's straps, it exploded into a room-size pile of denim that his friends called Mount Levi. "Those jeans were in horrible shape," Brit recalls. "Full of holes, ripped up." Rather than ship them overseas, he spent his nights patching the jeans and his days trying to sell them at flea markets, three pairs for $10. Profits were skimpy. "It was absolutely the lowest point of my life," he says.

But Brit noticed something unusual at the flea markets. Some vintage dealers would inspect his stacks of jeans and excitedly pluck out individual pairs for purchase regardless of condition. That's when Brit began to learn about big E's and little e's. Before 1971, Levi's jeans had an uppercase E printed on the tab sewn into the rear right pocket. After 1971, the company switched it to lowercase. In a general sense, a pair of Levi's is considered vintage when it has a big E, and these are much more valuable in the eyes of connoisseurs. (Vintage big E's are unrelated to Levi's premium Capital E line.) Brit learned about dozens of such categories for different brands, including classifications exclusive to the earliest types of jeans. He educated himself in the nuances of rivets, stitching, denim types, labels, and suspender buttons. "Jeans have their own language," he said. "It takes a while to figure it out."

Levi's is easily the most deep-pocketed consumer of vintage jeans. The company's historian, Lynn Downey, a self-described "obsessed vintage lunatic," explained that Levi Strauss effectively invented "jeans" when he began putting rivets into the seams of denim pants in 1873. In 1906, the company's four-story warehouse burned down after the great San Francisco earthquake, destroying their inventory. Currently, the oldest piece in their collection is from 1879. "Levi's has produced items that I've never seen," she said. This is a problem because vintage clothes represent the history of fashion and also mark the future. "Levi's designers are the primary users of our archives," she said. In 1996, the company launched its Levi's Vintage Clothing line, featuring replicas of recovered pieces. Brit has conducted a few deals with Downey, and he refers to her type of high-dollar denim as "big game."

Because Levi's didn't start selling jeans in the eastern U.S. until after World War II, there was an inherent limit to what could be found there. So in August 1997, Brit loaded his Jeep and migrated to Durango, Colorado. He began traveling up and down the Rocky Mountains until he knew the location and hours of just about every small-town thrift shop where someone might unknowingly drop off an item of surprising rarity and value. He would buy pickup loads of clothing at Goodwill prices and then sort out the more valuable items for shipment to his growing clientele of domestic and international vintage-clothing dealers. Jeans remained his passion, but he also developed an eye for other items that would get snapped up by savvy shoppers and Wild West enthusiasts: canvas work clothes, concho belts, biker jackets, hand-tooled cowboy boots, decorative saddle blankets, antique fur coats, riding chaps, cowboy hats, army surplus, and even homemade apparel.

Perhaps the most important thing Brit learned while hunting vintage clothes in thrift shops is that thrift shops are not the best places for guys like him to hunt vintage clothes. He didn't want the things that a person had recently quit wearing and donated; rather, he wanted the things that a person's great-grandfather had quit wearing and tossed into a dusty corner on a homestead, where it was forgotten about for a few generations. "I used to walk into a good thrift shop and my palms would get sweaty," Brit told me. "And then one day I couldn't get excited by thrift shops. It's like I used to enjoy firecrackers, but now it takes dynamite to get me high."