Sydney Opera House Pylon View

Exploring Sydney’s Hottest Hood – Chippendale

If thoughts of bare-bodied hunks gyrating to cheesy top hits come to mind when you think Chippendale, stop right there.

Or don’t. Who am I to judge?

Chippendale, the hottest district in Sydney right now, is not to be confused with the famous Las Vegas male striptease performers, also known as the Chippendales.

Once passed over as just an inner-city, working-class district of Sydney, the area that is bordered by Broadway and  Cleveland Street is now home to the coolest restaurants, boutiques and galleries in Sydney.

In fact, start the day by getting your fix at The Old Clare Hotel. Singapore’s favourite hotelier, Loh Lik Peng, who has opened several gorgeous boutique hotels around the world, is behind The Old Clare and his signature touch can be seen everywhere.

Those familiar with his group, Unlisted Collection’s, hotels will recognize the upcycled vintage items they are known for, like the dentist’s chair and retro light fixtures.

Sydney Old Clare Hotel Dentist Chair

Sydney Chippendale Old Clare Hotel Bar Me

Sydney Chippendale Old Clare Hotel Sofa

Sydney Chippendale Old Clare Hotel Bedroom

Even if you’re not planning to stay there, grab a drink at the hotel’s marvellous bar or better yet, get ready for a meal.

And where else but the restaurant that has been creating waves in the Sydney scene, Automata. Headed by Chef Clayton Wells, formerly from Momofuku Seibo, the ever-changing set menu at 2-hatted Automata sees his playful take on seasonal ingredients come to life.

This is where I learned to appreciate Jerusalem artichoke and I can still taste that ridiculously creamy yoghurt dessert!

Stave off the post-lunch zombieness by eating some more. Some more chocolates, that is. Buy them at Kakawa, and have a cuppa next door a Glider KS Café; they allow you to eat those chocolate treats with their coffee.

Sydney Chippendale Automata Artichoke

Sydney Automata Fish

Sydney Automata Dessert

Sydney Chippendale cafe

Next, start the gallery/shops walking route – must-visit is The White Rabbit Gallery. A private museum borne out of the owners’ love for modern Chinese art, the exhibitions are at once quirky and thought-provoking.

Sydney Chippendale White Rabbit Hanging Man 2

Sydney Chippendale White Rabbit echidna display

Sydney Chippendale White Rabbit teahouse
Teahouse at The White Rabbit Gallery

Other stops along the way include Press Books (116 Abercrombie St) and Galerie Pompom (2/39 Abercrombie St).

After all that mental stimulation, it’s time for some tummy satisfaction. Without a doubt, the prettiest desserts in town can be found at Koi.

Ex-MasterChef contestant and dessert maestro, Reynold Poernomo is behind this and if you were astounded by his whimsical creations on the show, you must grab dessert here!

Sydney Koi Dessert Bar

Sydney Chippendale Koi Interior

After tea, round two of the walking workout starts and be sure to check out the exhibits at The Old Rum Store (2-10 Kensington St) and Kensington Contemporary (32-34 Kensington St).

And you might think you’re done with Chippendale by now, but there are still a couple of restaurants worth trying for dinner, and they include Kensington Street Social and 2-hatted Ester. Make reservations in advance.

But, if you’re looking for something a little less fancy and lighter on the pocket, head for Spice Alley – I spotted prata and teh tarik there!

Sydney Chippendale Spice Alley

Sydney Chippendale Kopitiam

It’s easy to spend a day out enjoying Chippendale and if you have 3 days in Sydney, check out my Food and Art Lover’s Guide to Sydney! Also, my list of Top Free Things to do on a Sydney stopover!

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