Red Wing, the century-old brand known for its premium work boots, is in the middle of a modernization effort. Along with a newly remade website and buzzy fashion collaborations with the likes of Fendi, the brand has released several big top-of-funnel marketing campaigns in the last year, making it far more vocal in 2025 than it has been in the past. Even creative director Aaron Seymour-Anderson said the recent marketing push is atypical for the brand.
The brand’s latest campaign, debuting next week, is called “Boots Drop The Hard Way.” It was designed by its creative team, along with the creative agency Wieden+Kennedy, to highlight the most valuable Red Wing customer — tradespeople — and to offer critiques of both the prevalence of drop culture in footwear and the growth of generative AI.
The campaign comes in three parts: a series of six billboards erected around the country made entirely out of materials like leather or wood and built by real tradespeople who work with those materials; an accompanying social campaign highlighting the builders of the billboards by name and featuring their work; and a contest to break open a series of stoutly built “shoe boxes” made from concrete, rebar and metal.
The latter is where Seymour-Anderson said the critique of drop culture comes in. Red Wing will open applications in the next week for certified tradespeople to use whatever tools necessary to break open three heavy-duty shoe boxes. If they can succeed, they’ll win free Red Wing boots for life. The contest itself will also be filmed and used for social content. Red Wing will pick from the applicants later this month, and the contest will be held in January.
“I’ve been collecting footwear for 30-odd years,” Seymour-Anderson said. “We wanted to subvert the idea in the culture of making everything as easy as possible. It shouldn’t be about who can be the fastest with a credit card or who can use a sneaker bot to scoop up a limited product before everyone else.”
The criticism of sneaker drops is especially timely for Red Wing as it continues to grow both its classic tradesman customer and its newfound fashion customer. For example, streetwear blogs like Highsnobiety have called Red Wing “the world’s best work boot.” But Red Wing CEO Allison Gettings has previously said that the brand is wary of getting too invested in high fashion, fearing becoming “too trendy” could be a negative for the heritage brand. In 2008, Red Wing launched a lifestyle division that handles projects like the Fendi collaboration.
Seymour-Anderson pointed to a cultural trend of “taking the easy way out” that Red Wing wanted to stand against. He cited the prevalence of cheap, easy shortcuts, like generative AI, and also cheap, low-quality products as examples. For example, a series of Apple ads from early in 2025 was widely criticized for pitching AI as an excuse to be lazy and inconsiderate. In contrast, Red Wing’s campaign is meant to celebrate the real, handmade and necessary things in life, and the people who make them.
The campaign concept fits well with Red Wing’s value proposition. At $300 a pair, there are far cheaper options for people in need of good work boots. Seymour-Anderson said the brand leans into messaging around “good boots that will last for decades” to entice people who may not normally buy high-priced apparel to purchase the boots. Red Wing repairs tens of thousands of pairs of boots each year. The popular subreddit r/BuyItForLife, where users recommend products with high durability and long lifespans, has dozens of posts about Red Wing boots that are still usable after 20, 30 or even 50 years.
“We really try to tell a value story,” Seymour-Anderson said. “You can buy a cheap pair of boots that will last one year, but then you’ll need to buy another pair. Or you could buy a more expensive pair that will last decades. That’s the pitch, but the reality is that people do have less money to spend. So we’re trying to keep our prices in check as much as we can.”
Like many brands, Red Wing has recently had to increase some prices. In May, its footwear prices rose by $15, while its accessories increased by around $6. Although Red Wing boots are manufactured in the U.S., they use parts and materials sourced from overseas, which increases costs. Red Wing is a privately held company and doesn’t disclose revenue. It is sold in over 1,000 doors across the U.S., including at fashion retailers like Nordstrom and work-supply stores like Berkeley Supply.
Other recent Red Wing marketing campaigns have trended in a similar direction, emphasizing the value of premium-priced boots. A summer campaign called “Will Your Wings” highlighted the heirloom nature of a good pair of Red Wings, with special “To” and “From” tags that could be sewn into the insides of boots handed down.
“The biggest thing brands can do to stand out and cut through the noise in marketing is to have a unique point of view,” Seymour-Anderson said. “With the business environment being as challenging as it is, it’s easy to play it safe. But if you do that, you’ll sound like everyone else.”
