Osklen began operation in 1986, when a group of Brazilian snowboarding enthusiasts decided to climb the Aconcagua, the Americas’ highest mountain. At the time, it was hard to find athletic clothing in Brazil that was suitable for extremely cold environments. Responding to this need, Oskar Metsavaht, a sports medicine specialist and one of the mountain climbers, created the Storm Tech System, a fabric permeable to transpiration and protective against cold, and designed a range of snow jackets.

The climbing was broadcast on TV, and the clothes became famous. Oskar Metsavaht gained further publicity when he became the first Brazilian to scale Mont Blanc. Then, in 1989, Metsavaht founded the Osklen brand. The company opened its first store in Búzios, Rio de Janeiro, offering a winter sportswear collection. Though the company started out selling cold-weather clothing in a warm-weather environment, in a few years, it expanded the product line into a ‘lifestyle’ fashion line that includes laid-back, surf-inspired aesthetics and an environmental focus.

In the 1990s, the Búzios store gained a reputation for innovative and high-quality clothing. In 1991, the company introduced Brazil to snowboarding fashions and designed a new coat line featuring high-technology. In 1992, the first Osklen fashion show took place at the Golden Room of the Copacabana Palace hotel in Rio de Janeiro where Metsavaht was given the ‘Rio Sul Award’ in the category, "Best Brazilian sportswear label." In 1996, Osklen introduced a surfwear collection. Oskar Metsavaht was invited by Chrysler in 1997 to design a limited Osklen edition of the Jeep Cherokee. In 1999, Osklen launched a women’s ready-to-wear collection.

In 2001, the Andy Warhol Foundation and the Coca-Cola Company invited Metsavaht to re-interpret some of Warhol’s drawings in a Brazilian way. In 2002, with the help of biologists, Metsavaht created ‘e-brigade’, an educational group of environmental activists and launched an accompanying line of clothing made of recycled materials.

Metsavath, who has no formal training in fashion design, designs the Osklen brand. He says he does not think of himself as a fashion designer, but as an artist who develops collections through a creative process, as if shooting a movie with Osklen’s clothes serving as the costumes. He presents them each season with a specific lifestyle motto. Together with his brother Leonardo, a prominent Brazilian professor and orthopedic surgeon, Metsavaht directed and produced a film trilogy named ‘Surfing the Mountains’ about two brothers searching for the best snowboarding mountains in 2007 that also influenced his fashion designs.

Metsavaht and Osklen were featured in an episode of Brazil’s Next Top Model in 2008 and also in America’s Next Top Model Cycle 12 Episode 11. Metsavaht shows his collections at São Paulo Fashion Week.

These days, Osklen offers its merchandise through 41 stores in Brazil, three each in Portugal and Italy, and one each in the USA, Japan, and Switzerland. The company also sells through showrooms in Italy, France, Spain, Greece, and Portugal.