The Heritage Collection: Retro-Chic Winter Boots

Black and White Cougar Original Pillow Boots

Canada’s iconic Cougar Pillow Boot gets a reboot! This signature style, which remains a best-seller 44 years after it was launched, has inspired next-generation collections destined to become new classics.


Written by Christy Wright, Guest Editor

An air of innovation surrounds the family-owned Cougar Shoes, an iconic brand that put Canada on the map as a footwear trailblazer. And, like all great brands, its backstory is as compelling as its designs – think young man arriving in Canada and starting a family business that would become a runaway success.

“When my dad and uncle created Cougar, they also created an icon: The Pillow Boot,” says Cougar Co-owner and Vice President Ron Sedlbauer. “Today’s Canadian consumer is either someone who wore the Pillow Boot as a kid or is a next-generation customer who is drawn to the signature shape, puffy detailing and directional take on fashion.”

Influencer with long red hair sitting on blue couch wearing Cougar Original Pillow Boot in Tan

Photo credit: @theseptemberinc

His brother Steve, Cougar’s President and Co-owner, is in complete agreement and firmly in the former customer category. “I was in high school when the Pillow Boot came out,” he says. “It immediately struck a chord. As more people wore them, more people wanted them. Initially crafted for practicality, they became ‘the look.’ You wore them two ways: laces wrapped around the ankle or tied loosely with the red tongue hanging out.”

The next iteration that inspires cool styling options is Cougar’s latest addition: the white Pillow Boot.

Influencer wearing black jacket and pants walking down steps outdoors wearing Cougar Original Pillow Boots in White

Photo credit: @brainsandbronzed

“Every two or three seasons winter-white re-emerges as a fresh fashion statement,” says Steve. “It struck me to try a white version of the Pillow and to make it a little more sophisticated with a black sole, lining and hardware.” This monochromatic beauty is a deft melding of bold style and almost makes you wish for snow. Steve says, “It just feels like fun to me and I think it will appeal to anyone who plans on going out and having fun this winter.”

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Watch: Alexis Honce reviews the new Pillow Boot Collection

The white Pillow shares the newness spotlight with the Prescott, which Steve describes as a fashion hiker, and the PAX, a more fashion-forward take on the signature style. “The PAX is definitely more contemporary and playful,” says Ron. Fashionistas take note: the metallic silver PAX started waiting lists. In fact, it’s something that Steve’s son Austin, who is on the design team, predicted.

Black and Silver Cougar Original Pillow Boots

As always, the new collections deliver the same excellence in craftsmanship. The quality – special tanning techniques, laboratory testing, high manufacturing standards – is hallmark; the tagline – Always Waterproof – reassuring.

And while the brand has thoughtfully expanded its styles and collections (parents will swoon at the new kids’ line), the Pillow Boot remains definitive and informative. “As we design new styles today and analyze fashion trends, we always look to our Pillow Boot DNA for inspiration,” says Steve. “Our Prato Sandal, for example, is a mule style on a platform sole with a puffy, super-soft leather upper, which is a definite nod to the Original Pillow Boot.”

Overhead view of Cougar Leather Prato Leather Sandal in Rose on concrete tile

Photo credit: @heysarahdarling

Ron’s son Brendon, who is on the marketing team, feels it’s come along way since the high school corridors of The Seventies. “Today’s digital world enables us to utilize visual assets to help connect with the next generation of Cougar consumers on a global scale,” he says. “Our ability to leverage engaging content across our Cougar website, newsletter, and social channels as well as with our retail partners' platforms has been a driving force behind our success in today’s digital climate.”

Other than making the Pillow Boot of the 2000s completely waterproof, the original hallmarks are still in place – think rounded toe and classic textured calf-leather with padded shaft and quilted detailing. “We even make them today with the 1974-launch-date logo and the factory label from the Seventies,” says Ron.

Christine Carlton wearing Cougar Original Piillow Boots in Tan in dark blue jeans and wool socks in snow

The Pillow’s line list of accomplishments is long: over 8 million pairs sold and being named one of the top 10 most iconic fashion moments by Canadian Living Magazine are just two examples. The fun part though is the reality. “I feel a great sense of pride every time I notice people out enjoying wearing Cougars,” says Brendon. “Whether it’s on the streets of Park City during a Sundance Film Festival, at a retailer event or just an everyday run to the grocery store, it’s always a thrill.”

Austin never forgets the impact of the heritage Pillow. He says, “Our entire product range stands for a level of quality and satisfaction that we aim to meet, or exceed, in terms of delivering to our customers. But the Pillow specifically inspires design details that are identifiably Cougar.”

Influencer wearing black jacket and pants walking down steps outdoors wearing Cougar Original Pillow Boots in White

Walking on a cloud

“Right now I’m loving the just-launched Pillow Boot to add bold hit of style to my fall outfits while keeping functional for everything from work to running errands to those daily quarantine walks I’m back to doing. [These] boots are on-trend AND temperature rated for -30°C.” – @brainsandbronzed

Influencer lower body walking outside in black jeans, red and white mits wearing Cougar Original Pillow Boot in Black

Dressing for winter weather

“These new Pillow Boots from Cougar have been my go-to. They are insanely comfortable, retro-inspired, have just a hint of red in the lining, and really kick up my winter outfit game!” – @gentrilee

Influencer sitting outside sweater and hat, with leather leggings and Cougar Wahoo Nylon Winter Boot with PrimaLoft® in Black
The warmest pair of boots

“The iconic Pillow Boots are guaranteed waterproof and can handle temperatures up to -30°C!!! They’re also very comfortable with fleece lining and have memory moulded insoles. I can’t wait to sport these boots all winter long!” – @allstylelife

If you want stylish boots with the benefits of modern footwear technology, look no further.

Grab a piece of Canadian heritage, and stay warm this winter!