Orchard Road lacks character and is no longer a draw as a shopping strip alone - that is the opinion of many shoppers interviewed by The Straits Times.
The precinct should reposition itself as a lifestyle and entertainment destination, some said, following news last month that the authorities are conducting a study for a blueprint to guide the area's long-term development.
On Singaporeans' wish list: more activities, outdoor and green spaces, cultural centres, nightlife, live music and 24-hour offerings.
For some consumers like operations manager Eu Chong Keng, who visits Orchard Road nearly every weekend with his family, the once-buzzing street has lagged behind other shopping districts like Hong Kong's Causeway Bay and Japan's Shibuya.
"Shopping these days is not about buying stuff but the experience... being at the centre of activities all day and night," said Mr Eu, 38.
But much of Orchard Road is dead after 10pm, while "Mustafa or Nex are bustling with much more life", he said, referring to malls in Little India and Serangoon Central respectively.
Plans to refresh Singapore's premier shopping belt, which faces competition from e-commerce and heartland malls, were announced last year.
Outdoor events and activities are among ongoing initiatives, with longer-term plans to make the road more pedestrian-friendly, including the possible reduction of vehicle lanes.
Teacher Teng Tse Sheng, 44, said he hoped to see the 2.2km stretch go car-free, with more greenery, alfresco dining and picnic spaces with playgrounds for children.
IT professional Tony Serio, 52, said that Orchard Road's malls house "some of the best shopping and restaurants on the island", which still serve many tourists and locals.
But Orchard Road is becoming "steadily outdated and in need of major design changes", such as the addition of greenery, water features and malls with open-air designs, he said.
Some, like business owner Peter Tan, long for Orchard Road's heyday, when it was a "fun district where people came to see and be seen".
"Now it seems so sterile and boring... We need to bring fun back into the equation," said Mr Tan, 40.
Mr Decry Hardiyanto Zaidi, 43, frequented Orchard Road in his teens for people-watching, window-shopping and nightspots like Fire Disco and Hard Rock Cafe .
"Now if you ask me, is there really a need to go there? Shopping - online is cheaper. Food - we can find plenty in (the) heartland. Sightseeing - what's there to see (besides) the Christmas lights?"
Having family-friendly features like a theme park, retailers that offer exclusive products and competitive prices, and a 24-hour shopping mall could draw crowds again, said the senior assistant engineer.
Local culture is what makes other famous shopping streets in cities like Tokyo and Bangkok stand out, said Cushman & Wakefield's research director Christine Li.
Orchard Road must find its own unique differentiation, and "future shopping malls will have to integrate the element of play, as many retail transactions will no longer be in physical stores", said Ms Li.
At least one mall has stepped up efforts to bring the buzz back, with Orchard Central's opening of 24-hour Japanese discount store Don Don Donki last month drawing shoppers at all hours.
The mall saw a "significant increase in footfall" for the month, said Ms Mavis Seow, chief operating officer of Far East Organization's retail business group.
Hokkaido Marche, a hybrid restaurant and foodcourt concept, will open by the end of the month, said Ms Seow.
"We welcome the new initiatives that support Orchard Road's betterment... Stakeholders could also adopt a differentiated positioning or an all-encompassing experience that integrates entertainment and shopping for their malls," she said.
Ms Angie Ng, head of business and projects at Nanyang Polytechnic's Singapore Institute of Retail Studies, said that retail precincts worldwide are facing similar challenges.
Noting that Orchard Road's last major revamp was in 2009, she said it is timely to upgrade its infrastructure and offerings.
"Retailers should harness technology and data analysis, while malls must work together to create a draw at each part of the street," she said. "Every stakeholder must play his part, otherwise other precincts will catch up."