Meet 19 Midwest companies thriving again by keeping it old-school as they craft hats, boots, watches and more.

Custom bikes under construction at Heritage.Odds are, you probably won't be driving a locomotive through Michigan's Upper Peninsula in winter anytime soon. But, for the sake of argument, let's assume that trudging across a shopping mall parking lot in February has roughly the same effect on your exposed earlobes. In which case, you want someone like Ida Kromer on your side.

Back when Teddy Roosevelt was president, Ida's husband, Stormy, spent his days leaning out a locomotive door, minding the tracks ahead as they disappeared into the north woods. As a sometime baseball player, Stormy worked in an old ball cap, which winter winds delighted in yanking from his head. So one day, he plopped one of his caps on the table and asked Ida for some R&D. Being a resident of the upper Midwest-which is to say, a resourceful type-Ida didn't need long to add a higher crown and a pull-down ear band that kept the lid firmly on Stormy's head.

That was 1903. By 1919, Stormy and Ida were in the hat business full-time with a humming Milwaukee factory. For a century hence, the woolen "head furnace" known as the Stormy Kromer has been protecting the noggins of generations of laborers, tobogganers and now even fashionistas who use phrases like "fashion forward."

Stormy Kromer hats.
Stormy Kromer hats.

Much of the Kromer's appeal, along with moisture-wicking natural fibers and throwback Elmer Fudd style, is the fact that, were you so inclined, you could drive up to Ironwood, Michigan, and meet the folks who made your hat. That's the secret sauce in today's era of farmers markets and microbreweries, when shoppers value a chat with producers almost as highly as the products themselves. And that has made a whole group of Midwest companies trendier than a fitness-tracking watch-just for staying the course they set in the horse-and-buggy days.

In some ways, America is a bit like a folk singer that strikes it big with songs of the simple things and then starts longing for the honest, hardworking life they left behind. As America's middle class arose in the 20th century, who didn't want the affordability delivered by mass-produced goods? But in time, our closets full of inexpensive stuff left us pining for something a little more ... thoughtful.

Maybe you can get by with a nylon briefcase from the big-box store. But for a moderate investment, you can head to work with a canvas-and-leather bag handmade by a craftsperson like Carole Evenson at Duluth Pack in Minnesota. Sure, the bags are overbuilt compared to what the daily commute requires. But when you upgrade to the products on these pages, it's for far more than performance. You're plugging into the mystique of the original Duluth Pack-those oil-scented canvas bags toted by generations of paddlers on Boundary Waters trips they never forgot. Lift a Duluth Pack briefcase to your nose on any given weekday morning and inhale. Hello, loon calls and gurgling swoosh of wooden paddles. Who couldn't use that on Hump Day?

Duluth Pack.
Duluth Pack.

Keeping some of these heritage brands in your life proves inspiring in other ways, too. Maybe you're prone to worrying about getting older and the world changing out from under you. Does that make you obsolete?

Ask the Columbus Washboard Company, established in Columbus, Ohio, in 1895. In the mid-1950s, the company had every reason to feel like a brontosaurus watching a meteor streaking from the heavens. Families were counting the days until they could afford a washing machine. By the 1970s, Columbus was the only washboard company left. Since then, the firm has reinvented itself to serve the disaster-readiness crowd, musicians and folks who just like washboards on their wall. The company even hosts a Washboard Music Festival every Father's Day weekend in Logan. When the market hands you lemons, make bluegrass music.

(Clockwise, from top) Allen Edmonds shoes, Estwing hammer, Clay City Pottery bowl, J.W. Hulme wallets and bag, Wolverine boot, Columbus Washboard.

Spotting the good stuff is just as critical at Red Wing boots, operating since 1905 along the Mississippi River in Red Wing, Minnesota. Charles Beckman's goal of making "truly good shoes" still isn't easy 110 years later. The company's most senior employees tend to be cutters, who visually judge each piece of leather (made at a company-owned tannery). The strongest leather pieces go where the boots need it most. Blemishes go out of sight. When you lace up your new Red Wings, human hands have touched the boots up to 200 times before yours. And you can return to the store for free monthly cleanings as long as you own them, even if you go in mostly for the coffee and conversation. That's a relationship that's hard to buy at the big-box store.

Horween Leather

Each time you watch an NFL or NBA game, you're seeing Horween at work. Its leather stars in pro sports' game balls and many Major League Baseball gloves, plus luxury products from several companies in this story (including Allen Edmonds shoes and Defy bags). Sole survivor of Chicago's once-teeming tannery industry, the company has occupied the same building since 1920. Want proof of Horween's bona fides? Their leather chemist comes from a family with 400 years of industry experience. "The big guys do it cheaper, and the little guys do it better," says fourth-generation owner Skip Horween. "We're one of the little guys. Our customers appreciate what we do."

Horween Leather.
Horween Leather.

Companies about to light 100 candles

1 Four presidents have taken the oath of office wearing Wisconsin-made Allen Edmonds shoes since the company began in 1922. So you can count on them to add a little extra gravity to your presentation at the next sales meeting.

2 Chippewa's engineer boot became an icon for bikers in the 1950s. James Dean never really goes out of style, but just to prove they're in synch with current pop culture, the company founded in Wisconsin in 1901 (the boots are made in Missouri today) now makes a line for J. Crew, among others.

3 We can't promise an Estwing hammer will always dodge your thumb. But if any tool has the elegant heft and balance to make you work more smoothly, this one with the leather-wrapped handle from a company founded in Rockford, Illinois, in 1923 is it.

The century club

Brands seasoned with 100 years of keeping customers happy.

Faribault Woolen Mill, Faribault, MN, est. 1865 From World War II troops huddled in foxholes to families watching sunrises on the cabin porch, Faribault blankets have warmed them all. On tours of the plant along the Cannon River, visitors see the process that turns raw wool into colorful blankets, throws, scarves and more. Visitors touch the wool, walk the creaky floors and browse a sleek retail shop full of jazz music, artsy lighting and company lore. For our couch, there's no substitute for the classic merino wool red blanket with black stripes.

Clay City Pottery, Clay City, IN, est. 1885 Justin Lewicki, only 27, figures he has enough local clay behind the shed to outlast his career, even as he hand-turns 100–300 new bowls and casseroles each day. The sixth generation of Griffiths to run the company (his mom is the other employee) works partly in a cabin that was on the place when his family bought it in 1885. His top seller? The 10-inch cobalt blue pie plate. "People say it makes a great pie crust," Justin says.

John Boos & Co., Effingham, IL, est. 1887 Blacksmith Conrad Boos made a side business of cutting local sycamore at his Effingham shop. One day, he placed a piece of sycamore on three legs to absorb his hammerblows, inspiring a passing butcher to request his own. Conrad's son, John, adapted the idea, and things went pretty well from there: If you spot a wooden butcher block in a home or magazine, you'll probably find the Boos logo branded on it. You'll get an instant dose of kitchen confidence just from working on a classic like the 18-inch round maple cutting board.

J. W. Hulme Co., Saint Paul, est. 1905 Students of Saint Paul history know that the awnings shading many of the city's classic homes came from John Willis Hulme, a one-time titan of canvas. The company expanded into many types of bags over the years, but faced financial ruin during the 2008 recession. Down to four employees at one point, Hulme has bounced back and now has craftspeople from every continent but Antarctica at work in Saint Paul crafting briefcases, backpacks and handbags. For a classic look, try the large Legacy leather handbag.

Wigwam, Sheboygan, WI, est. 1905 If you're looking for a sock to trust your feet to, polar explorers and professional distance runners seem like a good bunch to ask. Wigwam's socks have proven favorites of soldiers, Ironman competitors and travelers who just want a comfy afternoon hike. (The company's wool swimming suit, on the other hand, didn't survive to the 21st century.) And who knew that this company gets the credit for adding colored seams to socks as a way of indicating sizes?

Wolverine, Rockford, MI, est. 1905 A company throws down the gauntlet by naming its product "the 1000 mile boot." But Wolverine's signature line, introduced in 1914, proved as good as its title. A modern anniversary collection revives the original 1000-miler's design in a variety of incarnations. The work boot version keeps the original's blue-collar cred rolling. But the lineup also includes choices like a wing tip and a ladies' Oxford style that are all suitable even for those who don't run a chainsaw or climb utility poles for a living.

Brand-new old-school

Three Midwest businesses driving the future with an eye on the past.

Heritage Bicycles, Chicago, est. 2011 Key fact in community launching: Caffeine never hurts. When Mike and Melissa Salvatore moved back from New York to build bikes (the first made in Chicago since Schwinn left in the '70s), cycles were just one element. "Companies are more approachable when they offer food and drink," Mike says. So while you're dialing in the details of your Heritage bike (like the swoopingly elegant Jane), you can get a great latte on the side. It's no accident that hanging out around Heritage's handmade tables feels like joining friends. Mike and Melissa host monthly employee dinners, and the couple's 3-year-old, Bennett, is both company mascot and inspiration for the Heritage Littles pedal-free kids' balance bikes. Six-hundred bikes in, the formula is working. In 2015, Heritage will open another shop in Nashville, Tennessee-and a stand-alone Chicago coffee shop.

Custom bikes under construction at Heritage.
Custom bikes under construction at Heritage.​

Shinola, Detroit, est. 2011 When the subject is Detroit's surging entrepreneurial streak, Shinola comes up often. After four years in operation, the company, which specializes in high-end watches but also makes bikes, clothing and leather accessories, has become Exhibit A that the city's heart still pulses with creativity and manufacturing know-how. "What Detroit stands for is really important for a brand like Shinola," says CEO Steve Bock, who unfailingly wants to talk more about Detroit and Shinola's employees than himself. The company (named after a once-famous brand of shoe polish) now employs about 350 and has stores in cities including Detroit, Chicago and London. Each watch features precision Swiss components, but is assembled in the Motor City. Betting on a market for watches made by hand in the Midwest's industrial heart may sound risky. But so far, America has proven Shinola right.

Defy Mfg.Co., Chicago, est. 2008 Chris Tag likes a little healthy rebellion. Who says you can't love your job? Who says American manufacturing is over? Who says you can't build a bag you think is truly amazing in your spare time, sell it to a guy on the commuter train and launch a company from there? Answer to all of the above: Not Chris. Leaving his job in the advertising industry, he set up Defy's headquarters in the Ravenswood neighborhood, a haven for artists, breweries and distilleries. Defy builds its bags tough; company literature frequently preaches that "life's too short for cheap buckles." The industrial-chic bags have caught on globally, with about half of total sales coming from customers overseas. "We get letters from all over the world telling us that we've inspired them to start something," Chris says.

Pop-up markets

Even in the online retailing era, new companies, especially those selling textiles and other tactile goods, know there's little substitute for letting customers touch the wares. In 2009, Mac and Katherine McMillan launched Pierrepont Hicks out of their home, selling ties, clothing and now a popular parka line. Soon thereafter, they started looking for other vendors to join them in forming pop-up markets that set up for a few days in roving locations. Saint Paul's J.W. Hulme bags signed up for the first market in Minneapolis, and soon requests came in to showcase handmade goods in other cities. Northern Grade markets carrying 20–40 brands of men's and women's clothes, coffee, spirits and music have now been held across the Midwest and the country.

4 cool things we heard reporting this story

When carrying a Duluth Pack canoe bag through the woods on your back, it's easier if you use a "tumpline" across your forehead to distribute the weight.

Ben Affleck dropped thousands of dollars in a Shinola shopping spree while filming the new Batman movie in the Detroit area last year.

Columbus Washboards still serve their original purpose among Amish communities and military personnel, who sometimes deploy without laundry facilities.

When Allen Edmonds supplied Barack Obama with a pair of shoes to wear at an inaugural ball, they renamed them "Hyde Park" after his Chicago neighborhood.

Buying guide

See the resources for the products in our pictures.