Several North American Sikh millennials are creating online values-based fashion enterprises that seek to encourage creative expression, self-determined representation, gender equality, and ethical purchasing, while steeped in the free market economy. Exploring the innovative ways young Sikhs of the diaspora express their values and moral positions in the socio-economic sphere, one finds many fashionistas, artists, and activists who are committed to making Sikh dress accessible and acceptable in the fashion industry. Referred to as “Sikh chic”, the five outwards signs of the Khalsa Sikh—the “5 ks”—are frequently used as central motifs for these businesses (Reddy 2016). At the same time, many young Sikh fashion entrepreneurs are designing these items referencing contemporary style and social trends, from zero-waste bamboo kangas to hipster stylized turbans. Young Sikh women are challenging mainstream representations of a masculine Sikh identity by creating designs dedicated to celebrating Khalsa Sikh females. Drawing on data collected through digital and in-person ethnographic research including one-on-one interviews, participant observation, and social media, as well as fashion magazines and newsprint, I explore the complexities of this phenomenon as demonstrated by two Canadian-based Sikh fashion brands, Kundan Paaras and TrendySingh, and one Canadian-based Sikh female artist, Jasmin Kaur.