Red Wing to Give Away Boots for Life to 3 Lucky Tradeworkers Through New Challenge

Red Wing is continuing its “Made the Hard Way” global campaign with a new challenge to win boots for life.

For its new “Boots Drop The Hard Way” initiative, Red Wing is challenging qualified tradesworkers to open sealed concrete, steel, and rebar-caged shoe boxes, using know-how tools, for a chance to win the prize.

The 120-year-old American footwear company said that tradesworkers who are pre-approved with qualified skills, experience, and competency in managing power tools are given a chance to open the boxes for a limited edition, once-in-a-lifetime prize.

On Dec. 11, applications will open and the brand will share more details on when, where, and how to participate on @redwing Instagram. For now, the brand has disclosed that three lucky recipients will win Red Wing boots for life at an event this January 2026 in Brooklyn, N.Y.

To mark the launch of the challenge, Red Wing will debut the new “Made the Hard Way” campaign, which features real trade workers and real voices including structural welder Eric Reuter, electrician and welder Lex Abreu, apparel designer Greg Jackson, and custom metal fabricator Tyrome Tripoli.

Shot by director Leo Aguirre, the campaign was also made the hard way – shot on analog film, “representing the campaign’s ethos for craft, permanence, and tangibility,” the company said.

And in tribute to the workers who built its home city, Red Wing created a series of one-of-a-kind billboard installations in Minneapolis, Minn. made by local tradesworkers. True to the way they were made, each features the message, “Made the Hard Way.”

Red Wing noted that each billboard features materials chosen because of the brand’s connection to workers. Materials used in the activation include a billboard assembled from scrap leather sourced directly from Red Wing’s own tannery and a billboard made from lumber in collaboration with local carpenters.