Stapleton’s “You Should Probably Leave” passes a mind-boggling benchmark as joins forces with outdoor outfitter Filson for another cold-weather collaboration.
Durable gear fit for the road gains an entirely new level of authenticity in the latest Filson x Chris Stapleton collection, anchored by a hard-working jacket made from an archival plaid pattern. And as Stapleton’s “You Should Probably Leave” celebrates more than one billion streams on Spotify, the rugged collab arrives at the perfect time for seasonal layering.
The 2021 hit joins “Tennessee Whiskey” in Spotify’s Billions Club, giving Stapleton two songs with more than a billion streams each. Stapleton’s staggering achievement joins songs by fellow superstars Taylor Swift and Morgan Wallen, while the next chapter in the partnership between the legendary Pacific Northwest outfitter and the “All American Road Show” touring star adds another version of the company’s famed Signature Mackinaw Wool Cruiser to its lineup.
Made in Seattle and featuring hard-working 100 percent virgin wool construction, the formidable jacket is wind-resistant and insulating even when wet, while four front cargo pockets and a full back pocket bolster its utility, with each detail designed by Filson alongside Stapleton.
Stapleton was deeply involved every step of the way curating the new collection, hand-selecting the company’s archival brown-green-multicolor plaid fabric for the burly jacket, a design known as “Peppermint Patty” plaid, thanks to its distinctive green hue. The collection, which is rounded out with offerings including a Western-inspired bandana and a signature graphic tee and hoodie, represents “a collaboration rooted in appreciation for heritage and revival,” Filson said.
The “Traveller” rocker dabbles in varied pursuits aplenty, including his own backstage-approved whiskey inspired by the song of the same name, plus a tour-ready Filson Traveller luggage collection. Stapleton’s interest in heritage style notably includes boots designed in partnership with Lucchese for true head-to-toe appeal. Stapleton has famously worn Filson on the road and previously worked with Filson on a 2024 Mackinaw Wool Cruiser revival using a deadstock 1980s fabric in celebration of the 110th anniversary of the iconic silhouette.
The latest capsule collection deepens the partnership, adding a custom-developed Alaskan Guide Shirt approved by the country superstar. The assortment, Filson notes, leans on “dependable fabrics, historic patterns, and graphics inspired by his collection of vintage stamps and patches.”
In first debuting the 2024 collaborative jacket with the Seattle-based heritage brand, Stapleton called himself “a long-time admirer of Filson,” adding that “I saw an opportunity to collaborate and bring back an old pattern I loved,” Stapleton said at the time. “It’s rare people build things that last a real lifetime – I love Filson stuff because it’s made to live longer than I will.”
Stapleton certainly puts his gear through its paces, wrapping up the latest run of his “All American Road Show” tour in Lincoln, Nebraska while plotting an early December Ronnie Bowman tribute in Nashville to end the year.
His first announced show of 2027 sees him headline the Buckeye Country Superfest. To add a dash of rugged style to your seasonal outerwear rotation, seek out a hard-working jacket or dependable flannel from Filson and Chris Stapleton.
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