Snoopy has been a lot of things over the years: a World War I flying ace, a writer, a professional daydreamer and, of course, Joe Cool. He’s also become something of a permanent fixture in fashion.
From designer collections to everyday streetwear, the Peanuts beagle keeps finding new ways into our wardrobes. The latest example comes from Timberland, which has teamed up with Peanuts for a Holiday 2026 capsule celebrating Snoopy’s coolest alter ego.
The collaboration brings together two very different icons of American culture, but the pairing makes more sense than it might initially seem. Timberland has spent decades moving between workwear, hip-hop and streetwear, while Snoopy has managed to move just as comfortably between cartoons, pop culture and fashion. For this release, the focus is on Joe Cool, complete with his signature sunglasses and laid-back attitude, alongside his little friend Woodstock.
The centrepiece is a black version of Timberland’s classic 6-Inch Premium Waterproof Boot. The familiar silhouette gets red and white contrast stitching, a second set of laces and three exclusive collaboration hangtags. The collection also includes graphic T-shirts, a sweatshirt, a beanie and socks, with Snoopy and Woodstock appearing across the pieces. It’s a fairly straightforward collaboration, letting the characters do most of the talking rather than completely reworking the original Timberland designs.
Snoopy has always had a place in fashion
It’s easy to dismiss cartoon collaborations as nostalgia marketing, but Snoopy’s relationship with fashion goes much further back than the current wave of childhood-character merchandise. In the early 1980s, fashion designer Jean-Charles de Castelbajac was already dressing Snoopy dolls, alongside a number of major designers who were invited to create miniature outfits for the character and his sister Belle. The resulting Snoopy in Fashion exhibitions travelled internationally, bringing together names such as Issey Miyake, Fendi and Oscar de la Renta.
Since then, Snoopy has appeared in collaborations with brands including Chanel, Gucci, Levi’s, Lacoste, Marc Jacobs, Uniqlo and Coach. More recently, the Snoopy in Style exhibition has brought together another generation of designers, including BODE, Kith, Sandy Liang and others. Clearly, this isn’t a character fashion has any intention of retiring.
Part of the appeal is how easily Snoopy can change roles. His different alter egos give designers plenty to work with, but the character is still recognisable even when the styling changes completely. Joe Cool, in particular, has the kind of personality that translates naturally onto clothing: sunglasses on, confidence up, not particularly concerned with what anyone else thinks. There’s a reason that version of Snoopy keeps showing up on T-shirts and sweatshirts.
There’s also something refreshing about a character who doesn’t take himself too seriously appearing in an industry that can sometimes take itself very seriously indeed. A Snoopy graphic can be playful without making the whole outfit feel like a costume. And because Peanuts has been around since 1950, the character means different things to different generations. Some grew up reading the strips, others know him through memes, plush toys or the latest fashion collaboration. You don’t necessarily need to know the full history to recognise the appeal.
Joe Cool meets the Timberland boot
The Timberland collaboration is a particularly natural match for Joe Cool. The character’s relaxed attitude sits comfortably alongside the brand’s long-standing connection to streetwear, music and everyday style. The black boot also gives the collection a slightly different look from the classic wheat-coloured Timberland most people immediately picture, while the red and white stitching adds a clear reference to the Peanuts characters.
The Timberland x Peanuts Holiday 2026 collection launches on November 5, with footwear, clothing and accessories available through selected Timberland retailers and the brand’s online store. Snoopy might have been around for more than 75 years, but apparently he’s still got plenty of outfits left to try.
