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When work boots wear out, most of the time they head to the trash. For Red Wing Shoes, that’s not always the case. 

“We have a pair of Vasque boots that Martha Stewart wore,” said Clare Pavelka, corporate historian and archivist at Red Wing Shoes in Red Wing, Minn. “We also have boots in our collection of 

John Rukavina, who was an iron worker in Chicago

, and he put the spire on the Sears Tower.”

Over the decades, as Red Wing boots have evolved from workwear to fashion staple, customers have started sending their weathered boots back to headquarters. 

“They’re very emotionally attached to their product because they live their life in in these boots,” Pavelka said. “They can’t throw it away so, you know, sometimes they just send it back to us.” 

That loyalty and appreciation inspired the company to display boots from tradespeople across the United States and even Canada. This 

 stands in their flagship store above a staircase leading to the company museum and showcases boots that bear the wear and tear of master plumbers, steel workers, brick layers and the like.

But there’s one boot that rarely makes it out of storage. It’s a tiny black leather boot in their #933 style. It’s laces are rawhide and stringy. The leather cracks where the ankle would flex and pock marks with dirt pepper the bottom of the sole. 

“It says ‘Red Wing Boots,’ not ‘Shoes’ on the logo,” Pavelka points out. “This boot has the wear and tear of 50 years.”  

Nowadays, footwear from Red Wing Shoes can cost anywhere between $150 to $400. This boot was likely sold for $7.20 in 1949. But Pavelka said it’s not the age of the boot that makes it valuable; it’s the letter that came with it. 

Below is a transcript of the the letter, dated Sept. 6, 1996: 

I would like to enter these boots in the ugly boot contest! Actually, I thought you might like to see what your product looks like after almost 50 years.

These boots were bought for my first husband when he was 12 years old. He was born in 1937. When we married in 1962 I had never hunted and needed hunting boots. As luck would have it, these fit. I have been hunting in them almost every year since. However, this year’s dove hunting did them in.

I just have one question. How do you ever expect to make any money if your boots last 50 years!

 campaign, which honors the stories behind worn boots. People can stitch “tiny wills” into their boots to leave for a loved one. 

Pavelka said without the letter to tell Gentry’s story, the boot would be just another old shoe. But combined, it demonstrates the deep appreciation for solid work boots. 

“I would have loved to have met [Peggy]. I have a million questions for her, but unfortunately, I've never spoken personally with with Peggy,” she said. 

After sending the letter, Gentry never followed up to learn the fate of her boots, so when MPR News reached out 29 years later, her response was one of surprise.

”I'm just flabbergasted,” said 85-year-old Peggy Gentry of Austin, Texas. “I really had thought those boots went in the trash and had been forgotten long, long, long ago.”

Gentry was in her 50s when she sent her boot and that letter to Red Wing Shoes. She had no clue they inspired a campaign or that anyone still cared about them.

“I thought they might enjoy just knowing that someone really appreciated their boots and the wear that they’d gotten out of them,” she said. “And so I just sent it to them as kind of a little, ‘Hey, you guys do good work.’”

Today, she’s chief operating officer and chair of the board for 

. Her work involves supporting missions and organizations in Nicaragua that work in areas of health and education. Gentry also leads annual mission trips to the country. 

She said nowadays she has no one to go hunting with anymore. But she’s happy that her boots could leave behind a footprint and legacy.

Do you have a “Hand-Me-Down?” An artifact of your own with a compelling origin story? Let us know at MorningEdition@mpr.org and a producer will reach out to you.

Listen to this “Hand-Me-Downs” segment by clicking the player above.

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Lukas Levin

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Red Wing Shoes are known for boots so sturdy that customers wear them for decades. One pair, nearly 80 years old, is kept in the store archives. 

‘I'm just flabbergasted’: How a Texas woman’s hunting boot got a second life in Minnesota

‘I'm just flabbergasted’: How a Texas woman’s hunting boot got a second life in Minnesota

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