Our Cheat Sheet to the Best of Chippendale

This formerly grungy inner-Sydney suburb has undergone a cool conversion in recent years, with design-led food, fashion, architecture and a treasure-box art gallery. By Alison Boleyn.

Eat

Concrete Jungle

If you’re hoping for a bacon-and-eggs blowout, keep walking. This hot new Sydney favourite serves only halal and healthy dishes. Its all-day breakfast menu stars the Nourish Bowl (beetroot hummus, kale, avocado, sweet potato and quinoa with a tahini-and-tamari dressing) and the pretty Blue Majik Smoothie Bowl with blue algae.

Spice Alley

When this place gets busy, the lantern-lit strip transports you to a South-East Asian hawker market. Standout dishes include the Thai pork belly stir-fry from Bang Luck and Alex Lee Kitchen’s chicken laksa.

Olio Kensington Street

Housed in a restored factory with exposed beams, Olio Kensington Street serves Sicilian and Moorish fare by Lino Sauro, who sources olive oil from his family’s farm in Sicily. Sauro’s great love is seafood; yours might be, too, after the starter of charred and citrus-glazed octopus.

Drink

Bar Chinois

Paris meets the Orient at this terrace-house bar, where teapot cocktails are poured while Gangsta’s Paradise and Sweet Child o’ Mine play incongruously in the background.

Handpicked Wines

The cellar door of this wine company offers cheese platters, sure, but also events such as make-up workshops and oyster-shucking tutorials. Our favourite? Saturday’s one-hour yoga class followed by a wine-tasting session guided by the Handpicked sommelier.

Stay

The Old Clare Hotel

The Old Clare Hotel pairs a 1930s façade with industrial, sometimes kooky décor that includes exposed bricks, high ceilings and lamps built from antique machinery. There are 62 rooms, a rooftop lap pool and two restaurants, Kensington Street Social (chef Jason Atherton’s all-rounder is as inviting late at night as it is for a late breakfast) and Automata. At the heart of it all is watering hole The Clare, which retains an “old man’s pub” feel with ageing rock posters and artfully “stained” carpet.

Do

Hop to the gallery Do a guided tour of White Rabbit Gallery, Judith Neilson’s collection of sometimes subversive contemporary Chinese and Taiwanese art.

Get your sugar fix Kakawa Chocolates does dainty handmade creations, while Koi Dessert Bar serves delights by MasterChef favourite Reynold Poernomo. The Dessert Extravaganza at Eastside Grill is a decadent spread of crème brûlée, green-tea tiramisù and sugar-dusted berries.

Give your wallet a workout Ashley Lim sells handmade women’s shoes at Extraordinary Ordinary Day. Central Park is home to streetwear chains, the fortnightly Brewery Yard Markets and Daiso Japan, stocked with homewares, toys and crafts – some weird, some wonderful and most priced at a flat $2.80.