Winston directed the music videos for "Best Song Ever", "Story of My Life", "Midnight Memories", "You & I" and "Night Changes". He also oversaw the production of music videos for "Drag Me Down" and "History". He also produced the Apple Music documentary, Behind The Album, for Harry Styles. He was accused of plagiarism for his work on the "You & I" music video, by Australian band Clubfeet.
Since 2015, he has served as a producer for The Late Late Show With James Corden and has produced several awards shows including the Grammys and the Tonys.
In 2018, he began creating an American sitcom titled "Happy Together" which is loosely based on the time Harry Styles spent living at Winston's house while One Direction was on tour.
He is the son of Professor Robert Winston, and brother of Tanya Winston and Joel Winston. Harry Styles is godfather to Winston's daughter, Ruby.