[1] Holland is a graduate of the BA Journalism course at the London College of Communication[2] and has worked for the following publications: the teenage Sneak magazine (fashion section), Smash Hits and Bliss.

In September 2006 Holland designed a range of T-shirts that were worn by both Gareth Pugh and Giles Deacon as they took their bow at the end of their runway shows during London Fashion Week.

The collection, entitled "Henry Holland for Le Specs", featured sunglass models with names such as "Muffin Top" and "Blinders".

[citation needed] To mark Magnum's 25th birthday, Henry Holland has created a bespoke 1960s inspired dress complete with mimicked cracked chocolate made from layers of fabric and sequins.

[14] In Autumn 2008 and Spring 2010, Holland co-presented T4's flagship fashion and music series, Frock Me, alongside Alexa Chung and Gemma Cairney.

He was also another guest judge on the show Glow Up: Britain's Next Make-Up Star season 2 In February 2009, singer MIA wore his black-and-white, polka dot tulle mini-design while heavily pregnant at the 51st Grammy Awards.