[1] Hailwood worked for six years for Auckland manufacturer Casual Apparel, learning how to cut, grade, construct and screenprint tshirts.
[1] His 2015 "sports luxe" collection featuring intarsia roses and embroidered unicorns was inspired by George V's coat of arms, while his 2016 show used fabrics he designed to celebrate his mother's life.
[8][1] Hailwood designs have been worn by Lorde, on the cover of Billboard magazine, Tilda Swinton, Maggie Gyllenhaal, Paloma Faith, Wendy Petrie and Jacinda Ardern.
[1][9] In February 2023 Hailwood was accused of breaching intellectual property, when a Stuff investigation by Dana Johanssen found some of his designs appeared to be more expensive duplicates of those available from "fast fashion" sites such as Urban Revivo, Shein, ASOS and Alibaba.
[2] Hailwood defended himself against the intellectual property charges by saying that some websites may be offering “similar looking but lower quality products”, and that he used the same methods as other designers in the industry.