[5] After finishing school and a year of study at TafeSA, Vasileff went on to work for Di Fabio Brothers Tailoring in Adelaide where he learnt the tricks of the trade.

[2][6] His former high school teacher encouraged him to apply for a scholarship to Milan's Istituto Europe di Design in 2010 which he won despite limited Italian skills.

Being close to his family, Vasileff felt strongly about staying in South Australia to build his career despite many in the fashion industry telling him that he would need to move overseas.

[2] Vasileff's first couture collection based on the ballet Swan Lake, and garnered great success as he was invited to showcase at the Sydney Fashion Palette.

In October 2015 and 2016 Vasileff closed the Adelaide Fashion Festival[11] with two sold out Paolo Sebastian runway shows.

[19] In 2020, Paolo Sebastian debuted at Virgin Australia Melbourne Fashion Festival (VAMFF), but due to the COVID-19 pandemic Vasileff was not able to be there in person to witness the collection hitting the runway.

Paolo Sebastian designs have also appeared on the following television programs: The Bold and the Beautiful, Days of Our Lives, Home and Away.