In 1990, Charles and his younger brother Keith worked at their parents shoe store in Ang Mo Kio to learn the ropes of managing a shoe business, before opening their first store in 1996 at Amara Shopping Centre. Charles & Keith adopted a new business model for their label because they observed that the traditional model of selling shoes purchased from wholesale suppliers were unsustainable. To emerge from intense competition, the company started designing their own shoes in 1997 based on customers' feedback. This strategic move allowed the company to gain greater brand recognition from their target clientele. As the business grew the company cut out the middleman and began working directly with production factories.
Charles & Keith launched Pedro in 2005, which is a line of men's footwear. Their product range was increased in 2007 to include accessories such as belts and sunglasses and higher end products.
In 1998, Charles & Keith began to expand their operations overseas when they ventured into Indonesia and by 2015, they had 40 stores. In 2001, Charles & Keith opened an international venture in the Philippines, where by 2015, they had more than 30 stores. In 2004, the company ventured out of Asia and debuted in the Middle East with a store in Dubai, and another in Saudi Arabia in 2005. In 2011, the brand had over 230 stores across the world mostly based in the Middle East and Asia.
In 2011, LVMH (Louis Vuitton Moet Hennessy) invested in a 20 percent stake. At the time LVMH stated that they intended to expand Charles & Keith's presence with 40 or 50 new stores across India. By 2013 Charles & Keith had grown to over 300 stores worldwide, including locations in Africa, and in Japan, where they opened a flagship store in Harajuku, Tokyo and also other shops in Yokohama and Osaka. All the stores are company-owned unless local legislation forbids this, in which case the stores are run through a joint-venture arrangement. In 2015, the brand expanded further into Cambodia,Panama and the Dominican Republic.
In 2017, Charles & Keith launched a Winter 2017 collection, featuring a diverse range comprising minimalist, functional, sports-inspired and revamped vintage styles, in Qatar.
In 2004, Charles & Keith became the first company in Singapore to set up an e-commerce website in an effort to expand its business, allowing the company to offer its products where it did not have a brick and mortar storeIn 2016, Charles & Keith had announced its closure of all of its stores in Japan and redirect efforts to developing its e-commerce site.