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Beginning in 1857, the northern shore of Hong Kong Island (also known as Victoria City) underwent a series of reclamations under then-Governor Sir John Bowring. The first phase of the Praya Reclamation Scheme had a direct effect on this current street, which used to be known as Praya Central during the Colonial Hong Kong era. Bowring's plans were opposed by British merchants who held lands in the Central area, and in response, the government instead commenced work in land reclamation in the Chinese-populated Western District. By the time the reclamation was extended to Central, the newly reclaimed land in Western had already been settled, and there was a discontinuity between the two roads running along the western and middle portions of the reclaimed shoreline. Upon completion, the roads were named Bowring Praya West and Bowring Praya Central respectively. Another series of extensive reclamation projects began in 1887 under then-Governor Des Voeux. Upon completion in 1904, Bowring Praya West and Bowring Praya Central (which by then were situated inland from the shoreline) were respectively renamed Des Voeux Road West and Des Voeux Road Central per the orders of then-Colonial Secretary and acting Governor Francis Fleming during the Duke of Connaught's visit to Hong Kong in 1890. From 1942 to 1945, the road was renamed Showa-dori by the Japanese occupation government.

The name Shek Tong Tsui was derived from the nearby old quarry, or "Shek Tong" (石塘) in Cantonese. It was located around modern-day Hill Road and The Belcher's, and was used by the Hakka people since the 17th century. "Tsui" (嘴) indicates that the area was a headland. The area was first settled in 1880 by granite miners. In the early 1900s, Hong Kong Island's brothels were moved from Possession Point in Sheung Wan to this area under orders from the Hong Kong Governor Matthew Nathan. The place thus flourished as a red light district and came to its golden period. During this period, Chinese affluents in Hong Kong came to Shek Tong Tsui for entertainment, and numerous Cantonese opera theatres and Cantonese restaurants were founded in the area. It was known locally in the Cantonese phrase "tong sai fung yuet" (塘西風月), which means "good times west of the quarry". Brothels in this area inspired numerous novels and Hong Kong films, most notably Rouge (1987) which starred Anita Mui and Leslie Cheung. This golden period lasted until the ban of prostitution by the Hong Kong Government in 1935. However, during the Japanese occupation of Hong Kong, the Japanese military government relocated all Chinese brothels to the area, which was renamed as Kuramae (?前) by the Japanese. Again the area boomed, with about 500 brothels in the area at the time, but they could only serve Japanese agents since the lives under Japanese rule were too harsh to enjoy for commoners. After the Japanese retreat, the name of the area was reverted back to its Chinese name, as with the rest of Hong Kong. The British ban went back into place, and all traces of Shek Tong Tsui's amorous history were washed away by decades of urbanization.

Wan Chai was first home to the many Chinese villagers living along the undisturbed coastlines in proximity to Hung Shing Temple. Most of them were fishermen, who worked around the area near Hung Shing Temple overlooking the entire harbour. Hung Shing Ye, the God of the Sea, was one of the deities worshiped by the locals. With the growth of the British Hong Kong administration, centred in old Victoria, modern Central, Wan Chai attracted those on the fringes of society, such as coolies, who came to live on Queen's Road East. A focal point of development was Spring Gardens, a red-light zone. By the 1850s the area was already becoming a Chinese residential area