Bowles has worked with directors Armando Iannucci, Amma Asante, Oliver Parker, Roger Michell, Edgar Wright and Neil Marshall.

[1][2] In 2012 Simon Bowles designed Roger Michell's "Hyde Park on Hudson" starring Bill Murray, set in 1930s Upstate New York about a British royal family visiting the US and their stay with Franklin Roosevelt, shot entirely in the UK.

Simon Bowles worked with Amma Asante again on "A United Kingdom" which tells the true story of the relationship between Seretse Khama, the chief to be of the Bamangwato tribe in the British colony of Bechuanaland in the late 1940s, and a white, middle-class Englishwoman, Ruth Williams.

Simon Bowles won at the British Film Designers Guild awards in 2019 for his work on Universal Pictures Johnny English Strikes Again starring Rowan Atkinson.

Bowles designed The Son (2022 film) written and directed by Florian Zeller, starring Laura Dern, Hugh Jackman and Anthony Hopkins and is currently working on A Quiet Place: Day One created by John Krasinski, written and directed by Michael Sarnoski, produced by Paramount Players, Sunday Night Productions and Platinum Dunes.