Heritage Meets Hollywood: Top Celebrities in Red Wing Boots

Founded in 1905, Red Wing has grown from just a small bootmaker in Red Wing, Minnesota into one of the most iconic boot brands on Earth. With 2 million boots now produced each year, one could argue that the brand is even more of a cultural iconoclast than their wearers — but there have also been some very, very iconic wearers of these boots.

Various stars over the years have donned Red Wings to varying degrees of success, so lace up and join us on this journey — some of these looks might surprise you!.

Ryan Gosling
Ryan Gosling is well-known for embodying the kind of rumpled-and-cool style that’s befitting of an action star, and his outfits on and off screen regularly serve as inspiration for the rest of us.

He’s also probably the celebrity who’s the most associated with Red Wing Heritage boots — again, both on and off screen.

He's frequently spotted sporting Red Wing Moc Toes on the street, both the Classic Mocs and the 10875s with brown laces. But he’s even managed to make sure his character sports them: he was sporting the newer Hawthorne Abilene Moc Toes for just about every scene of 2024’s The Fall Guy, while his 875s were directly referenced in The Gray Man on Netflix.

Steve McQueen
Steve McQueen was an iconic American actor nicknamed the "King of Cool," celebrated for his rough-and-tumble charm and his starring roles in classic films.

Anyone who’s known for effortless style would of course wear Red Wings, and McQueen did so on the cover of a 1971 Sports Illustrated where he is pictured both shirtless and jumping an off-road motorcycle in his pair of Prairie 877s. (Cue the "how you think you look wearing RW's vs how you actually look" meme.)

It’s therefore only fitting that two generations later, his granddaughter Molly McQueen partnered with Red Wing for the limited-edition release of their Classic Moc, featuring his signature and racing number ‘278’.

Jack Nicholson
In what is perhaps Red Wing’s most infamous portrayal on the silver screen, Jack Nicholson’s not-at-all-a-character-you-should-emulate Randle McMurphy in One Flew Over the Cuckoo’s Nest wears an unmistakable pair of 877 boots.

As a rebellious but charismatic presence a generation before some others on this list, it is only fitting that his footwear would also be the 8-inch grandpa of the Moc Toe, which has remained largely unchanged since its launch in the 50s.

Oprah Winfrey
Needing no introduction, the daytime-TV queen turned pop-culture icon made headlines — well, in her own outlets — when she debuted a unique look for the cover of O Magazine.

Adorned in a flowing red dress, a tawny teardrop fedora, and 3368 Sand Mohave Iron Rangers, what better way to prowl the Amazon rainforest? (Don’t answer that.)

Fans of Red Wing may know that the 1926 release called The Gloria was Red Wing’s first women’s boot, though it took another 90 years for the brand to release a Heritage line dedicated to women’s boots. Ending up on the feet of Oprah herself might be the real watermark of its enduring cultural status.

David Beckham
Not to be confused with the Beckman Red Wing boot, David Beckham has been seen wearing Red Wing boots on numerous occasions. Despite being an English football icon, Beckham doesn’t shy away from this American tradition, commonly integrating the 1907 6-inch Moc into his everyday wardrobe. He was also snapped riding a motorcycle in a pair of 877 Classic Moc Toes, but drawing comments about his unusual lacing method!

David Letterman
We are particularly fond of how Letterman styles the Iron Rangers in the latest season of his interview-based Netflix show “My Next Guest”. Reborn with a thick beard, he makes multiple appearances in his boots, made with the distinct Oxblood mesa leather. If you ask the Red Wing subreddit, they are convinced these beauties stole the spotlight from Dave Chappelle in their interview!

Bradley Cooper
Bradley Cooper has a few pairs of Red Wing Boots on rotation, including Iron Rangers, Blacksmiths, Moc Toes (of the Black Prairie persuasion), and who knows how many others he’s worn when he’s gone unstalked by paparazzi.

The Red Wings we associate with him the most closely are the ones he shouldn’t have worn: brown Iron Rangers with a charcoal suit. Pulling off two menswear sins at once — pairing work boots with a suit and brown boots with grey — is an impressive feat nonetheless, and certainly a testament to his love for the brand.

Kanye West
Known for his visionary contributions to the worlds of music and for, uh, some more questionable contributions to public discourse, Ye has always headlines for his fashion and was spotted here in a fittingly distinct choice of Red Wing.

Eschewing the moc toe that’s more common in hip hop, Ye is instead rocking the black style 3059 Men’s 17-inch Pac boots. Built for freezing temperatures, these safety work boots somehow straddle the worlds of high fashion and energy-sector work. After being photographed in them numerous times, secondhand-market prices have skyrocketed for this rare model that is no longer produced.

Drake
The music megastar Drake has also been spotted rocking Red Wing boots, specifically the Moc Toes. In his 2010 album Thank Me Later he even brands his ‘OVO crew’ as the "Red Wing Boot Gang".

Spotted in the same pair as some of the other celebs on our list, the 1907 Heritage Moc Toes, he nonetheless brings a more contemporary streetwear-influenced style that compliments the classic boot well. For our money, the brand’s moc toe is their product that best fits into a streetwear wardrobe, and Drake seems to agree.

Wrapping it up: Why Celebrities Choose Red Wing Boots
They’re high quality and longlasting, but we’d venture to say that it’s the way Red Wing combines these qualities with timeless good looks that makes them such enduring symbols of Americana. Whether a classic pair of Moc Toes or something more niche, what better way to develop a parasocial relationship than through hyper-analyzing your favorite star’s choice of Red Wing?

Words by Nick English