Sydney's wild inner west is a chaotic maze of crowded streets and smoky bars (at least in those places where the anti-smoking laws have yet to be applied), where every other person is pierced or has a menacing dog in tow. Don't be afraid, though—it's for show. Newtown is a great promenading neighborhood, with all the hallmarks of a college town (the University of Sydney has a campus nearby), including miles of cafés, music venues, and vintage furniture stores. The area has long been a stronghold of the city's gay and lesbian community, but in a more low-key way than flamboyant Darlinghurst. Weekends are the best time to visit.
The 1,600-seat Enmore Theatre (130 Enmore Rd.; 61-2/9550-3666), housed in a legendary Art Deco building, has seen its fair share of boldfaced names; patrons who were lucky enough to snag tickets are still raving about the intimate gig the Rolling Stones played here on their 2003 tour. Other recent headliners: Alicia Keys and Chris Isaak. • The equally cherished Bank Hotel (324 King St.; 61-2/9565-1730), one of many traditional pubs in the area, serves authentic Thai food in its beer garden. • The Peasants Feast (121A King St.; 61-2/9516-5998; dinner for two $62) is devoted almost entirely to food that is delicious and virtuous. Try the organic pork belly with eggplant caviar, or the slow-roasted free-range duck with spiced red cabbage and grilled apple. • Furniture hunting is a popular sport in these parts, particularly along the King Street strip. Newtown Old Wares (439 King St.; 61-2/9519-6705) is packed with mid-century finds, such as arc lamps and kidney-shaped coffee tables. • If blowing the dust off old treasures isn't your thing, take a detour to Prettydog (1A Brown St.; 61-2/9519-7839). This eclectic fashion boutique used to specialize in vintage clothing but has since evolved into a showcase for up-and-coming local designers, as well as more established names like Karen Walker and Nicola Finetti.
THE DRESS CIRCLE
There are few better ways for a dedicated retailaholic to spend a Saturday than browsing the stretch of Oxford Street from South Dowling Street to tony Queen Street. But the path less traveled (at least by those not wearing Manolos) is just off this busy thoroughfare. William Street, with its tiny footpaths and Victorian shop fronts, has a distinctly European flavor, and patrons dress the part in Prada and Jimmy Choos. While these narrow streets are a magnet for young style devotees who know their Burberry from their Balenciaga, the area is also popular with the pearls-and-twinset contingent, breezing in from moneyed Woollahra, just streets away. Deeper into the heart of Paddington, the shopping and café precinct Five Ways is made for stylish loitering; Sydney's literati and media whiz kids have made this crossroads their own.
In one of the city's best fashion melting pots, the silk slips and hand-embellished gowns at Collette Dinnigan (33 William St.; 61-2/9360-6691) share a postal code with the work of big-name, cutting-edge Belgian designers—such as Dries Van Noten, Veronique Branquinho, and Walter Van Beirondonck—at Poepke (47 William St.; 61-2/9380-7611). • Andrew McDonald Shoemakers (58 William St.; 61-2/9358-6793) creates bespoke footwear popular with fashionable brides and men looking for one-of-a-kind loafers or classic brogues. • Just William Chocolates (4 William St.; 61-2/9331-5468) is a third-generation family business that has won the hearts and stomachs of Sydneysiders. The exquisite handmade chocolates could put an end to any diet, although the svelte young things that populate this stretch give the impression that they abstain. • Belinda Menswear (29 William St.; 61-2/9380-8873) is the newest addition to the street, and the youngest in Belinda Seper's Sydney empire. Her first menswear store stocks Helmut Lang, Marni, Yohji Yamamoto, Martin Margiela, and Rick Owens. • Down the hill, Leona Edmiston (88 William St.; 61-2/9331-7033), Australia's answer to Diane von Furstenberg, specializes in flattering day dresses, mainly in jersey and silk.
The madding crowds tend to thin out a little as you move away from Oxford Street, giving you a real feel for the neighborhood. Squint and you might mistake Five Ways, the convergence of five streets some three blocks northwest of William, for a particularly sunny Parisian arrondissement. Gracious Victorian terraces give way to a small but perfectly formed shopping precinct with glittering glimpsesof the water (listen for the occasional foghorn, issued from far out at sea). • Here you'll find a French pâtisserie, La Gerbe d'Or (255 Glenmore Rd.; 61-2/9331-1070), that rolls out wickedly buttery croissants; a traditional pub, the Royal Hotel (237 Glenmore Rd.; 61-2/9331-2604); and Parlour X (213 Glenmore Rd.; 61-2/9331-0999), a fashion-forward boutique stocking labels like Vivienne Westwood and Cacharel. There are also several cafés, a day spa—the Paddington Beauty Room (217 Glenmore Rd.; 61-2/9356-8700), known for its addictive La Prairie facials—and a fine wineshop, Five Way Cellars (4 Heeley St.; 61-2/9360-4242), that carries many hard-to-find vintages. • Come Saturday, the Paddington Markets (395 Oxford St.; 61-2/9331-2923; www.paddingtonmarkets.com.au; Saturdays 10-5) roll into town. A sprawling clothing, jewelry, and craft showcase that takes over the grounds of the Paddington UnitingChurch, this is where you'll spot burgeoning talents in design and art, so snap up their creations while they're still at bargain prices. Many of Australia's best fashion labels—Zimmermann, Third Millennium, Bracewell, Paablo Nevada, and Lisa Ho—got their start here.