For other designers, the city-state's quirky lingo, known as Singlish, is what makes the Southeast Asian nation unique. A mishmash of English with words and phrases from Malay and Chinese dialects including Hokkien, the distinct tongue is a beloved part of the Singaporean life that, for most of the time, leaves foreigners baffled.
Published this month, "The Strangely Singaporean book" written by the Little Drom Store goes beyond common Singlish words such as "kaypoh" to explain over 100 phrases such as "blur like sotong" (commonly used to describe someone in a world of his own) and "stylo milo" (a local stand-in for 'You're so cool'). The new publication builds on the store's previous 'Strangely Singaporean' merchandise collection, which has been a best seller since its launch last December.
"We were inspired by our previous project [because] while doing it, we thought there must be more of these phrases. After talking to our parents and the older generation, we realized there were sayings like ' song song gao jurong' that we don't use anymore so we added them [into the book]," said Little Drom Store co-founder Antoinette Wong. "Song song gao jurong" is a Hokkien phrase used to describe utmost satisfaction.
Read MoreNostalgia wave hits Singapore's F&B scene
Nostalgia is also a key theme, with some entrepreneurs saying that the country's 50th birthday marks a special time to look back at Singapore's transformation from a colonial trading post into a first world country within one generation. As such, celebrations for the Golden Jubilee should involve a re-connection with the simpler pleasures of yesteryear.
That's the concept behind "Game of Chope", a board game playing a pun on the name of popular U.S. television series "Game of Thrones" and largely based on the rules of a nostalgic favorite called "Aeroplane Chess."
Launched by design studio and brand WhenIWasFour last month, the game sets players on a mission to reserve a restaurant or cafe table using their Game of Chope game pieces instead of packets of tissue paper that in real life play a key role in a common practice called "choping", or reserving a table by leaving a tissue packet on it.
"With the availability of smartphones and the internet, technology is always around and for me that has led to a lack of social interaction and [relationships] have become very cold. So I wanted to use these nostalgic [board games] to bring back memories and encourage people to engage in more meaningful bonding activities," the chief designer behind WhenIWasFour, Li Ling Tan, told CNBC. "That was also one of the reasons why I started the brand six years ago."