4th April 2025

Jasper Trumble’s life has been anything but conventional. A commercial helicopter pilot, Jasper’s career has taken him around the world, from flying in the UK, America, throughout Europe to navigating the skies of India, his professional journey has been a testament to his passion for precision, adventure, and excellence. But it’s not just the skies that have captured his attention; leather—specifically bespoke footwear—has long been a fascination passed down through his family lineage.

Growing up with a grandfather who owned a leather tannery in the UK, Jasper was steeped in the world of leather from an early age. It was no surprise that he developed an enduring interest in leather products, finding himself captivated by the craftsmanship, texture, and timeless appeal of well-made leather goods. Whether it was a beautifully crafted leather bag or a pair of shoes, the art of leather was something he was always drawn to.

While flying for nearly two years, transporting Indian politicians and VVIPs around the state of Maharashtra, Jasper’s curiosity about bespoke footwear took root. During this time, he encountered a family of shoemakers in Pune, a bustling city rich in culture and history. The family specialised in making custom shoes, and Jasper, eager to have shoes crafted to his specifications, began commissioning bespoke pairs. Through this experience, he not only gained quality footwear but also developed a deep connection with the family, envisioning them as potential suppliers for his future endeavours.

However, despite their dedication and skill, the shoemakers in Pune were unable to meet the level of craftsmanship Jasper envisioned. It was a realisation that would set the stage for his next big move. Rather than accepting compromise, Jasper decided to take matters into his own hands. With strong ties to Italy, a country revered for its centuries-old shoemaking tradition, he set his sights on the Le Marche region, the epicenter of Italian shoemaking.

Le Marche, known for its artisans and luxurious craftsmanship, would become the birthplace of Jasperosso, Jasper’s custom made footwear company. The region’s centuries-old traditions of leatherworking and shoe crafting mirrored his own values of precision, quality, and attention to detail. After finding the right shoemaker in Le Marche, Jasper knew he had found the perfect match. Here, his vision for a company that offered custom-made sneakers, built to order and personalised to the client’s taste, would come to life.

As Jasper immersed himself in the world of Italian footwear, he observed an emerging trend—the growing demand for customisation and personalisation in fashion. Customers were no longer content with simply buying what was on offer; they wanted to personalise and customise, reflecting their personal style and preferences. This insight led to the development of the three dimensional configurator, a cutting edge piece of technology that allowed clients to design their own shoes online. Much like his experience in India more than a decade ago, Jasper realised that he was once again bringing a vision to life, but this time, with the power of technology.

Today, Jasperosso stands as a fusion of old world craftsmanship and modern innovation. By combining the finest leather with the ability for customers to create their own custom sneakers, Jasper has built a brand that reflects his passion for both quality and personal expression. With a strong commitment to providing not just custom made sneakers, but a personal experience, Jasperosso’s shoes are not simply a product, they are a testament to a journey that started with a helicopter pilot’s quest for the perfect pair of shoes.