Troy's first job after University was with Emilio Cavallini, where Troy started as an Assistant designer. At the conclusion of the first year Emilio suggested that Troy go work in the major fashion studios in Empoli and helped him find a job with the head designer of Hugo Boss and Calvin Klein. Two years later Troy returned to become associate and finally head designer.

Designing with Emilio was to be the Avant Garde. Visionary not only as a designer, but also as an Artist, Emilio was open to new ideas daily and expected the unexpected. The production facility was next door to the factory making rapid prototyping the absolute expectation. Working directly with the technicians on the Santoni tubular knitting machine, Troy was able to create a series of Photoshop scripts to create dynamic and innovative knitwear. Client focused design meant interviewing the best clients and designing to their needs and desires.

Troy made multiple mens and womens collections of approximately 72 garments each collection twice a year with Emilio for the four years they worked together.