Henry Holland was born in Ramsbottom, Greater Manchester and attended the London College of Communication. He gained attention with his bold, 1980s-inspired T-shirts that displayed catchphrases such as "I'll tell you who's boss, Kate Moss" in the 2000s; Holland subsequently designed a full collection and founded his own fashion house.
He was listed number 23 in the Pink List 2012. The Pink List citation said:
- "Holland has gone from strength to strength since founding his label with a small collection of printed T-shirts in 2007. Holland's collaborations with Debenhams, Levi's and Kickers, among others, mark him out as an entrepreneurial presence within British fashion."