According to the bank, this logo represents the four caissons supporting the foundation of its first headquarters, the DBS Building Tower One at Shenton Way. Its early corporate literature has also claimed the logo to have been created by one of the bank's founding leaders soon after the bank was founded on 16 July 1968. However, architect of the DBS Building, Lim Chong Keat, has also claimed credit for the design. These two accounts are disputed because the first instance the logo made its appearance was in 1972.

A third possible origins of the logo is offered by graphic designer Yew Wei-Lee. He claims to have created the logo while working for BEP Akitek when it was developing DBS newest property development, the Plaza Singapura shopping mall, which opened in 1975. His account is supported by Yew's colleague Yang Soo Suan, who said the mall's project architect YC Wong had then solicited for logo proposals from various architects in response to a logo request from DBS chairman Howe Yong Choon.

Howe eventually chose a proposal with four hearts representing each of the bank's service motto, which Yew was then asked to refine into the actual design. According to Yew, he saw his logo as representing the Development Bank of Singapore to be at the centre of the crossroads, with all four directions pointing towards it.

In 1982, the logo was modified as part of a rebranding exercise led by Landor Associates.