Despite not joining Made in Chelsea until the second series, the charms and unconventional fashion sense of Oliver Proudlock, better known as simply Proudlock, has thrust him to the forefront of the show often throughout his tenure on the series. Appearing uninterrupted from the second until ninth series, Proudlock missed Made in Chelsea: LA, and took a hiatus from the series, though has appeared briefly in Series 10.
Proudlock has served on several occasions as an unintentional love rival to his close friends, notably with Caggie Dunlop as a rival to Spencer Matthews, though he later dated her cousin Alice Davidson instead, and with Sophia Sassoon to his housemate Francis Boulle. He also clashed briefly with Jamie Laing over his secret dating of Lucy Watson.
Outside of these storylines, Proudlock's "bromances" with the other male cast members has become a popular part of the series, leading to several parodies and celebrations at End of Season episodes. Initially being part of Spencer, Jamie and Hugo Taylor's group, he soon developed a close friendship with Francis, and moved in with him and Jamie, becoming "The Lost Boys." Upon moving out, he struck up a similarly close bond with Stevie Johnson, the two becoming known as "The Bowery Boys." The two remain housemates, though Stevie no longer features within the series and Proudlock's hiatus means his appearances are limited.
- Main article: Series 5
The series begins with Proudlock and Jamie caught up in Spencer's feud with Francis. After Jamie's hotel party, Proudlock meets with Jamie and Spencer and tells him they're going to live with Francis. He also reveals Sophia has contacted him, revealing she was unsure of her feelings for Francis and has left the country. He later attends Andy's birthday gig in Camden. The next day, Spencer confronts Proudlock, Jamie and Francis at the estate agents' about the housing situation, though they've already signed contracts on Proudlock's insistence they go ahead with their plan anyway, and Spencer angrily walks out on his two best friends. At Proudlock's studio, Josh Coombs comes in to pick up his stuff after being fired, though the two remain friends. He also meets with Spencer, apologising to clear the air, though Spencer blames Jamie primarily about the housing situation. Later, in their new house, Proudlock encourages Jamie and Spencer to make up, though Spencer still voices his concerns over Francis.