Orchard Road and Marina Bay are undoubtedly some of the best places to check off your shopping lists in Singapore, but if you’re seeking something truly out of the ordinary, Dempsey Hill proves to be a quiet gem.

For starters, in place of multi-storey malls are old army barracks, so you’re already in for a vastly different shopping experience. Built in 1860 under the British empire before its regeneration, these breezy, square-columned buildings remain to be a big part of our history today, although they’ve now been redesigned to house some of the most unique establishments the island — and region — has to offer.

From dapper furniture and locally-made truffles to cult fashion brands, here are all the unique shopping experiences you’ll find at Dempsey Hill.

Anjalichocolat

(Image credit: Anjalichocolat)

If you’ve ever wondered what it’s like to craft your own bonbons and truffles, local chocolatier Anjalichocolat’s retail boutique at Loewen Road in Dempsey Hill offers workshops that teach you the finer art of tempering and making your very own. If you want to skip the making and go straight to the eating, the space also sells Anjali’s now-famous creations— the perfect after-meal treat, we think.

163 Tanglin Rd, Singapore 247933; Tel: +65 6509 6800

Dover Street Market Singapore

(Image credit: Dover Street Market Singapore)

Since its opening in 2017, Dover Street Market Singapore has become the playground for any fashion enthusiast in the region, especially since it’s one of only six in the world, and the only one in Southeast Asia. The massive space is home to cult favourites like Sacai, Wales Bonner, and Jacquemus, as well as big brands names like Gucci and Vetements. Today, the multi-label boutique continues to draw crowds with its limited edition exclusives, as well as its stunning seasonal installations.

18 Dempsey Rd, Singapore 249677; Tel: +65 6304 1388

Siri House

(Image credit: Siri House)

It’s not often that a single space in Singapore offers all the makings of an afternoon well spent, but Siri House at Dempsey checks all the boxes with ease. Set deep within the enclave’s lush greenery, the establishment is a one-stop destination for good food, design, retail, and art, and is the only one of its kind in the world besides Bangkok. 

If it’s a hearty, unforgettable meal you’re after, Siri House offers elevated comfort dishes by Head Chef Leo Pang, such as the Jam & Toast — inspired by our local kaya toast — and Bikini, a sandwich featuring a trio of cheeses, cured meats and truffle tomato sauce on toasted milk bread.

 The Shop At Siri House is a retail space that’s constantly updated with new vendors selling trinkets and clothing from Thai designers, while the adjourning art space sees a rotation of intriguing exhibitions by local and regional artists.

8D Dempsey Rd, #01-02 Dempsey Hill, Singapore 249672; Tel: +65 9487 1552

Timothy Oulton at Curio

Driven by an inherent affection for British heritage and a keen eye for detail, Timothy Oulton’s unique brand of eclecticism sits in perfectly at Dempsey, with furniture and interior decor that could transform any home from drab to fab. There is, after all, a reason why members’ club 1880 chose to furnish its dapper 22,000-square-feet space with his designs. His outpost at Dempsey Hill is the only one in Southeast Asia besides Bangkok, and offers a spectrum of both new and signature pieces, including his award-winning and hand-crafted tomcat chairs and aviator-inspired pieces.

14C Dempsey Rd, Singapore 249687; Tel: +65 6479 7619

Spa Esprit

(Image credit: Spa Esprit)

Nestled amidst the greenery is the sanctuary that is Spa Esprit, a home-grown brand that’s now a household name thanks to its pampering array of services. Besides facials and massages — which will no doubt be a fantastic way to wind down after a day of shopping — the Beauty Emporium also offers beauty products from cult labels like Malin+Goetz and Two Lips, alongside the full in-house beauty and body line.

8D Dempsey Rd, #02-00, Singapore 249672; Tel: +65 6479 0070

Redsea Gallery

(Image credit: Redsea Gallery)

Founded in 2001, Redsea Gallery is one of Singapore’s leading contemporary art galleries, with a curation of captivating Asian creations by regional emerging and established artists. Like the other shopping spots on this list, the gallery is housed in one of the revitalised colonial British army barracks, and supports artworks across a diverse range of mediums including painting, sculpting, and photography. Shop for pieces not found elsewhere here. 

Block 9 Dempsey Rd, #01-10 Dempsey Hill, Singapore 247697; Tel: +65 6732 6711

Dempsey Hill has always been a neighbourhood known for its spectacular food offerings, but there’s so much more to the heritage-rich enclave than meets the eye. Whether you’re seeking something extraordinary or simply need a respite from the bustle of Orchard Road, Dempsey Hill has all the makings of a stellar shopping destination in Singapore.

Shatricia Nair
Deputy Editor
Shatricia Nair is a motoring, watches, and wellness writer who is perpetually knee-deep in the world of V8s, tourbillons, and the latest fitness trends. She is fuelled by peanut butter and three cups of coffee a day.