Disembark at either NS22 Orchard or NS23 Somerset MRT stations. On CityBuzz, the bus stops along the shopping district on route C1-#8 (Paterson), C1-#9 (Tang Plaza), C1-#10 (The Heeren) or C1-#11 (Peranakan Place). The choice is yours!
Orchard Road is a shopping district which name has become a household name not only in Singapore but in Asia as well (I know this because any shopping places in Malaysia tend to be compared to this few-mile-long strip).
There are a lot of shopping malls for anyone to memorize by heart, even by yours truly, and visiting all of them will take you probably 1-2 days. With years of flourishing appetite for locals and tourists to shop here, the malls have since ventured out of Orchard Road into its tributaries such as Tanglin Road with its Tanglin Mall, Tanglin Place, Tanglin Shopping Centre and Tudor Court (a unique colonial-style row of shop houses), and Scotts Road with Far East Plaza, Pacific Plaza and Scotts Singapore Centre (known for its designer boutiques like Pois Pois, Blush and local-bred Esther Tay).
But the real actions thrive in the heart of Orchard Road itself. If you are entering from Tanglin Road into Orchard Road, you will be greeted by the likes of Delfi Orchard (speciality: Waterford crystal and Wedgwood china), Forum the Shopping Mall (plays host to a Toys "R" Us mega store), Palais Renaissance (for ardent fans of DKNY, Versace, Jim Thompson, Prada and The Link), an Far East Shopping Centre. Sounds like a walletful, doesn't it?
Those are not even half of what Orchard Road has to offer! Venturing close to midway of the street will bring you to International Building (a bland name I must say but still offers many small boutiques and tailor shops), Liat Towers (with its anchor Esprit boutique), Wheelock Place (with 2 floors of marks & Spencer and a ground-level Borders book store) and Shaw House (with 4 floors of Isetan).
Tired yet? There are still plenty of malls to visit, seriously! Right in front of NS22 Orchard MRT station is Tangs Plaza (opened in 1932, this is one of the oldest malls in Singapore), Wisma Atria (mostly for apparel shopping like Isetan, Anteprima, Topshop and Warehouse), Lucky Plaza (made famous by Pua Chu Kang show but the mall itself is less than interesting), Ngee Ann City (perhaps the most crowded mall around with Takashimaya chain store located here, along with Guess?, Hugo Boss Woman, Zara of Spain, Mango, Country Road of Australia, and South East Asia's largest Kinokuniya!), The Promenade, The Heeren (made famous for HMV, the largest music store in South East Asia), Orchard OG, Orchard Building, Orchard Shopping Centre, Midpoint Orchard and Orchard Emerald (you think they could come up with with better, don't you?).
Finally we get to the "end" of Orchard Road madness with Centrepoint, among Singapore's biggest and most popular shopping centre where you can shop for everything under the sun, and Orchard Point.
My suggestion is that for you to plan what to buy and choose a few shopping malls for that purpose. Otherwise, a plain innocent window-shopping intention can suddenly turn upside down.
Amazing shopping district! Clean and organised strip of shopper's paradise.