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The first shop of note on Orchard Road was [[Tangs]] founded in 1934 and established on Orchard Road in the 1950s.
Orchard Road shopping malls do include [[ION Orchard]], [[Wisma Atria]], [[Ngee Ann City]], [[Orchard Central]], Orchard Gateway, 313 @ Somerset, Orchard Plaza, [[Plaza Singapura]], [[The Centrepoint]], [[The Heeren]], Mandarin Gallery, Cathay Cineleisure Orchard, [[Wheelock Place]], [[Liat Towers]], Shaw House and [[Scotts Square]].
Prominent tenants in the shopping malls include Don Don Donki (Orchard Central), Courts Nojima (The Heeren), Decathlon (The Centrepoint), Marks & Spencer (Plaza Singapura, Paragon and Wheelock Place), Rubi Shoes (ION Orchard), Cotton On (ION Orchard, 313 @ Somerset and Plaza Singapura), Castlery (Liat Towers), Melissa (Wheelock Place including a collaboration with Outside+ at ION Orchard), Zara (313 @ Somerset), Love Bonito (ION Orchard and 313 @ Somerset), Uniqlo (ION Orchard, 313 @ Somerset and Plaza Singapura), IORA (Wisma Atria and 313 @ Somerset), Takashimaya (Ngee Ann City), Sephora (Ngee Ann City, ION Orchard and Plaza Singapura), H&M (Orchard Building), [[Apple Store]] (270 Orchard Road which was opened in 2017)<ref name=":0" /> and Nike (268 Orchard Road, which was opened in 2024)<ref name="Sekkappan">{{Cite web |last=Sekkappan |first=Cheryl |date=2024-01-19 |title=A massive three-storey Nike store opens at Orchard Road today, the largest in Asia |url=https://www.timeout.com/singapore/news/the-largest-nike-store-in-asia-opens-at-orchard-road-today-011924 |access-date=2024-02-19 |website=Time Out Singapore |language=en-GB}}</ref>
Retailers have been closing down shops during COVID-19 pandemic, these include the American fashion retailer [[Abercrombie & Fitch]] opened a flagship store on Orchard Road on 15 December 2011, Forever 21 store at 313 @ Somerset, Zara store at Liat Towers, Topshop store at ION Orchard, H&M store at ION Orchard, Robinsons store at The Heeren and Bershka store at ION Orchard.<ref>{{cite web|title=Abercrombie & Fitch is too sexy for Singapore|url=http://travel.cnn.com/singapore/shop/abercrombie-fitch-too-sexy-singapore-833818|publisher=CNN|access-date=20 August 2013|date=29 September 2011|archive-url=https://web.archive.org/web/20130522185752/http://travel.cnn.com/singapore/shop/abercrombie-fitch-too-sexy-singapore-833818|archive-date=22 May 2013|url-status=live|df=dmy-all}}</ref>
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