Squire questioned the boundaries between design, fashion and art, pioneering a more open and broad spectrum of how designers were perceived to be able to work within other creative disciplines and mediums. Initially specialising in tailoring, Carlo used traditional Savile Row craft together with relevant modern design principles. It was during this period that Carlo started to work on unstructured tailoring, with the first ideas produced in 1999. Unstructured tailoring changed the way tailoring was seen, up until then full structured heavier suits with interlinings and horse hair chest pieces was the norm. Carlo wanted to design tailoring that was completely unlined and without internal structure, allowing the cut to dictate any external shape. The designs were lighter and more comfortable. He christened the work "Unstructured Tailoring" and the menswear industry has adopted this term to define all design of this nature. During this period Carlo worked as a freelance menswear designer for Burberry and Valentino in Japan. After five years of the concept work at Squire and having achieved all that he had set out to for this project, unexpectedly in 2003 Kilgour approached Carlo to become creative director. This project offered an opportunity to define and work on creating and building every element of a new Kilgour, a different ‘type’ of creative and artistic work. Carlo set the brief to create a modern hybrid menswear brand combining the craft and heritage of Savile Row with all aspects of modern current design. Carlo conceived the concept of the brand, controlled all design, designed the flagship spaces and the campaigns. The project was critically and commercially very successful with Carlo receiving many diverse plaudits and awards including British "GQ" Most Stylish Man and being voted Menswear Designer of the Year in 2005 by the British Fashion Council, the highest award achievable in this field. In 2008 Kilgour changed ownership shortly before Carlo's debut on the Paris catwalk in 2009, Carlo promptly resigned, leaving the brand he founded as Kilgour. In 2013 Kilgour changed hands again and the new owners approached Carlo to reprise his role as freelance creative director, the remit was to re-position Kilgour as an "International Contemporary Bespoke Brand and Tailor". In 2009 Carlo established his own studio working with clients privately as a consultant design and creative director. The studio also focuses on artistic work, his first sculpture solo show ‘Permanence 2010 - Travertine marble stone & gold’ opened on June 25, 2010 at RCM Galerie in Paris.