From glam girls to the nouveau grunge, everyone can find a personal cache of Sydney cool. Ian Lloyd Neubauer breaks down the ’burbs so you can tailor your itinerary to your attitude.

CLOCKWISE FROM TOP LEFT: Ferry traffic during the annual

Australia Day activities in Sydney Harbour; a curbside art dealer at one of Sydney’s many flea

markets; Dhaka-inspired Bang Street

Food; lunch under the sun at Jonah’s; QT

Sydney’s "director of chaos" concierge;

Sydney rock oysters at Otto Ristorante.

What’s Your Sydney Style?

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CLOCKWISE FROM TOP LEFT: State Theatre building in the CBD; QT Sydney’s barbershop; fashion godfather Peter Morrissey; seasonal French at Tetsuya’s; Paspaley’s Sydney flagship shop.

harbor, the beaches, the people? We’re all fiercely proud to call this bullet-speed, sun-kissed city home. But scratch beneath the surface and you’ll find we cut ourselves into clans. In Sydney, your credo is tied to the suburb in which you live. Elitist? In a way. But it’s also a key for successful living. Even as rule-breaking, trend-setting new venues keep opening, most of the attractions and distractions in this heaving metropolis of 4 million are still compressed into a small number of precincts and suburbs. Toss in the fact that transport to and from outlying areas can be costly and grindingly slow. So we subdivide: the super-chilled to the North Shore, the cooler-than-you to the Inner West, and the old-money types around the Harbour Foreshore. When planning a trip here, visitors should heed the Sydneysider’s lead. For example, for cutting-edge eats, you can’t go wrong with the Inner East; Mad Men redux can be found in the CBD. Let your style—and these neighborhood-by-neighborhood itineraries—be your guide.

THE CBD Sydney’s Central Business District gives new meaning to the term “stuffed shirts.” Enter a maze of specialist stores whose shopability is vouched for by Australia’s godfather of fashion, Peter Morrissey, who presides over several eponymous labels. Chinatown sits in the south, Darling Harbour in the west, the Royal Botanic Gardens on the eastern flank and the historic Rocks district in the north, meaning this area is basically the center of its own world.

Known as the “director of chaos,” the concierge at QT Sydney dresses like a character from A Clockwork Orange. The thespian service model blends with psychedelic digital art and baroque furnishings at this standout, 200-room hotel filling two neo-Gothic sandstone buildings. This is Sydney’s coolest, quirkiest and sexiest place to sleep. Combine your stay with a session at the hotel’s hammam-inspired spa, a chili-infused cocktail at the Boston-style Gilt Lounge, and oven-baked trout, lamb or duck at the Gowings Bar & Grill. If Don Draper were transported to Sydney in 2015, he’d feel right at home here.

Especially when he could procure two of his favorite vices nearby. Beautifully tailored suits and expensive whiskey are both served with élan at Shirt Bar, an innovative retail concept that blends old-world charm with espresso counter service. Secreted away on Sussex Lane, Shirt Bar is a smash among Wall Street types on Fridays after work. While you’ve got your wallet out, sashay over to the flagship boutique of Paspaley, the world’s leading cultivator of pearls, sourced from Paspaley family farms on Australia’s remote northwestern coast since 1935. Their oversize pearls encrusted with diamonds, rubies and emeralds make the ultimate Sydney souvenir.

I LIVE IN AUSTRALIA’S MOST BEAUTIFUL AND BOISTEROUS

CITY. OK, MAYBE I’M BIASED. BUT, COME ON: THE

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views will haunt your dreams for years to come. From here, catch a water taxi to Otto Ristorante on Cowper Wharf. This is where the A-listers come on sunny Sunday afternoons to consume the freshest Sydney rock oysters, the most succulent suckling pig and the chunkiest swordfish steaks—and to drown in champagne. Throw in paparazzo, skyline views and the salty scent of the sea, and you’ll see why Otto makes for a quintessential Sydney day.

THE INNER EAST Sandwiched between the CBD and Sydney’s exclusive eastern suburbs are a series of former working class barrios housing Australia’s most dynamic dining and nightlife precincts. This is the hottest ’hood right now for foodies and night owls.

Surry Hills is Sydney’s own Soho, a place where seedy old pubs, kebab joints and ridiculously expensive restaurants coexist. One of the loudest and more reasonably priced new additions to the area’s global menu, Bang Street Food, borrows from the fast food of the markets of Dhaka to create dishes with depths of flavor that are off the Richter scale. The A$55 “Bang for Your Buck” degustation tells no lies and includes Bangladeshi-born chef Tapos Singha’s world-besting honey-roasted paneer and drop-dead gorgeous mango ice-cream dessert rolled in white chocolate and pistachio nuts. From Surry Hills, walk eastwards to Darlinghurst via Oxford Street and on to Darlinghurst Road where you’ll find Eau-de-Vie—dubbed “one of the best cocktail bars in the world” by Gharbi. “They make drinks using liquid nitrogen and fire and all kinds of rare spirits.”

In the red light district of Kings Cross, Gastro Park is the restaurant laboratory of Grant King, Australia’s own Heston Blumenthal. Using bizarre ingredients like fish scales, kangaroo carpaccio and caramelized veal, the mad-capped molecular master chef creates inimitable concoctions like liquid butternut gnocchi in mushroom consommé and chocolate honeycomb spheres that crack open like dinosaur eggs to reveal a Technicolor treacle of sweets. Available only on Saturday, King’s 10-course degustation dinner matched with wines is off-the-hook decadent. A short stroll along Macleay Street will take you to Potts Point, a compression point of Art Deco apartments and Victorian terraces that stakes its claim as Sydney’s Manhattan. Among a cacophony of trendy cafés and bookstores is The Roosevelt, a former alehouse where mob boss Abe Saffron—a.k.a. Mr. Sin—held court in the 1940s. Today it’s a dimly lit Prohibition-style speakeasy with plush red carpet where Sydney’s latter-day cocktail king Sven Almenning and his co-conspirators serve drinks in glass pistols, high heels and hip flasks.

When daylight beckons, clear your head at Centennial Park, a voluminous expanse of wetlands, ornamental lakes, pine forests and playing fields on the fringe of the Inner East. In mid-November, just before spring becomes a delicious summer, Centennial Park hosts the super-exclusive Polo in the City. With reams of high fashion, horses charging down the field, corporate marquees and free-flowing champagne, this is a chance to mingle with Sydney’s well-heeled cool kids.

BONDI One might think that Bondi needs no introduction, but beyond the golden strip of sand that is Australia’s most visited beach is its most happening suburb—a global cooking pot of ever-changing restaurants, hipster cafés,

Keep the good times rolling with dinner at Tetsuya’s, a high temple of gastronomy that consistently rates as Sydney’s premiere fine-dining experience. Its success story harks back to 1989, when Japanese-born Tetsuya Wakuda opened the trailblazing degustation restaurant in an obscure spot in the western suburbs that over time became Sydney’s hottest meal ticket. Today Wakuda practices his trade—a marriage of French culinary techniques and seasonal local ingredients with an emphasis on seafood—from a heritage-listed CBD mansion crammed with ceramic Oriental art. Testuya’s signature dish of 20 years, the confit ocean trout, is requisite eating. Walk off your meal on George Street, says Morrissey, who loves going to the cinemas there—“gold class, of course.” The area “feels like Times Square because there are so many people around,” Morrissey adds. “It pumps after dark.” THE HARBOUR FORESHORE The playground of Sydney’s rich and beautiful spans from the ferry terminal at Circular Quay, to the waterfront mansions of Potts Point, to the hidden beaches and national parks of Vaucluse. This is the home of the city’s newest grande dame and global icons like the Sydney Opera House.

Don’t worry about being clichéd, and get your culture on at the Opera House, Morrissey says. “It’s such an extraordinary experience just walking in there. And The Sydney Theatre Company around the corner on Dawes Point is extraordinary for its ability to modernize the classic musicals and plays. The costumes and sets are absolutely cutting edge.” While you’re in the neighborhood, learn about the razor-wielding street gangs that terrorized Sydney a century ago at the Justice & Police Museum, a historical hideaway built inside a 19th-century police station and courthouse replete with holding cells and interactive installations.

From Circular Quay, ride the Eastern Suburbs ferry to Double Bay, a shopping village reminiscent of the French Riviera that’s home to the new InterContinental Sydney Double Bay, one of the only five-stars in this part of town. Set in the old Ritz-Carlton building, this beauty is awash with designer chandeliers, polished brass handrails and vast swaths of Calacatta marble. Winter at the InterContinental is best spent at the 1930s-style gin bar with its grand piano and roaring fireplace, or filling up on a Sunday roast at the Stockroom restaurant. Come summer, hit the roof pool for some serious cabana action and panoramic harbor views. After sundown head to Vine, a whitewashed restaurant and wine bar that pays homage to upscale home-cooking. Choose among lamb shoulder, New Zealand snapper or free-range pork—slow-roasted and served with delicately baked vegetables in stoneware dishes—followed by a dessert tasting plate featuring Valrhona chocolate soufflé and dulce de leche lollipops. Then party til late at Casablanca nightclub in Double Bay, where fixer extraordinare Karim Gharbi, owner of just-launched, money-is-no-object bespoke The VIP Sydney concierge service, runs a custom bottle service at private booths.

The following morning, ferry to Watsons Bay, a former fishing village with a Hamptons-esque feel that’s movie-set pretty. The action revolves around the Watsons Bay Boutique Hotel, a large waterfront venue on a fairytale of a beach lined with pastel rowboats. The Wato’s beer garden adds a touch of St.-Tropez to Sydney, with tropical drinks and accompanied by DJs on weekends. The suites upstairs are on the Spartan side but the harbor-window

CLOCKWISE FROM TOP: Whale Beach as seen from Jonah’s; off-field antics at Polo in the City; a molecular creation by Gastro Park’s Grant King; Karim Gharbi (right) creates bespoke itineraries for the jet-set.

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CLOCKWISE FROM BELOW: Polo in the City at Centennial Park; cabana action at the InterContinental Sydney Double

Bay; brilliant booze-in-a-boot at The Roosevelt; the city's skyline at dusk from Otto Ristorante.

The harbor-window views will haunt your dreams for years to come

bars and boutiques. This is city living at its best: the salt in your hair, lattes and margaritas, a healthy outlook and the high-end of everything.

“Kick off your day with a morning run from Bondi to Bronte along a track hugging the spectacular coast. It’s one of Sydney’s great joys and it’s free,” says Renae Leith-Manos, the editor emeritus of Bondibeauty.com.au. “Or, if yoga is your thing, the BodyMindLife studio in Bondi offers the ultimate physical and spiritual experience. Afterwards, Bondi Wholefoods is the perfect place for a healthy breakfast.” Pick up some sugar-free homemade brownies to go along with your choice of their natural beauty products.

Brown Sugar’s black stone eggs—a symphony of English muffins, hash browns, tomatoes, bacon and poached eggs—are rated by locals as the ultimate hangover cure, and wash down well with the signature house coffee, a secretive New Guinean-Guatemalan-Ethiopian blend. For live music on a sunny Sunday arvo, hit the Beach Road Hotel, then grab a craft beer at any number of Bondi Road’s bars after dark. For something somewhat more exotic try Mr. Moustache, a Mexico City-style cantina hidden within the Hall Street dining precinct. Mr. Moustache specializes in mescal, the complex and brooding agave-based cousin of tequila. The bar, as one can imagine, stocks hundreds of mescal varietals flavored with things like raisins, jalapenos, tamarind, plums and chilis. Your waiter or barman will then match each shot to an avant-garde array of tacos made from hibiscus flour and stuffed with baby octopus or braised pork. Round off your meal with the caramelized banana, a Bondi-Mexicana bespoke dessert set adrift in agave syrup, bathed in milk caramel and ablaze with liquor.

And now a drum roll please… at the very top end of Bondi’s food chain is Icebergs Dining Room, a cantilevered glass prism overlooking the southern end of the beach commanding cry-into-your-cocktail beach vistas. “Every celebrity who visits Sydney ends up there at some stage,” Gharbi assures. “It has the ultimate view.”

THE NORTH SHORE A more slow-paced world of red-brick Californian bungalows, long lonely beaches and left-of-field places to stay lies on the north side of Sydney Harbour. Escape the city bustle here with a laid-back day-trip or a more active adventure—not to worry, though, there are still spectacular hotels.

No visit to Sydney is complete without a ferry ride from Circular Quay to Manly Beach, a more down-to-earth version of sun-kissed Bondi on Sydney’s north shore that’s a mecca for surfers and Brazilian backpackers. From Manly, a string of sandy coves bookended by limestone rock formations continues for 30 kilometers up the coast before reaching a climax at Palm Beach. Backdropped by native bushland, this golden moon of sand is almost too beautiful to be true; little wonder it was selected as the set of the hit Australian sitcom Summer Bay. Begin your visit to

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Palm Beach with a refreshing swim in the surf or a short bush walk up to Barrenjoey Lighthouse on Sydney’s northernmost peninsula. Epic doesn’t even begin to describe the views you will see from here all the way to Ku-ring-gai Chase National Park, across Broken Head and the entire northern coast of Sydney.

For lunch head up to clifftop Jonah’s, overlooking neighboring Whale Beach, one of Sydney’s longest continually operating restaurants. Now nearly 90, Jonah’s boasts one of the city’s largest private cellars, with more than 6,000 bottles of vintage Australian and international wine. After sampling a few, you’d be advised to stay the night in one of the 11 Jacuzzi suites with endless Pacific views. At around the A$1,000 mark, boarding here isn’t cheap. But it’s only half the standard rate at La Corniche, a whitewashed penthouse footsteps from the water taxi berth at McMahons Point Wharf on Sydney’s lower north shore. From the Jetmaster fireplace, to the indoor pool, to the private lift and wrap-around windows with reach-out-and-touch-it views of Sydney Harbour Bridge, every inch of La Corniche screams Sydney excess.

Also on the business end of the north shore is Taronga Zoo. This expansive cornucopia of wildlife is known the world over for a reason and you don’t need to have kids in tow to love it. The Roar & Snore overnight experience combines a night safari, buffet dinner and camping. Rise in the morning for a cooked breakfast, behind-the-scenes tour and the zoo’s world-famous seal show.

THE INNER WEST Following a decade of speculator-led, hipster-fed gentrification, this once grungy collection of suburbs on what was until recently the wrong side of the town has emerged as Sydney’s new epicenter of cool.

So complete is the Inner West’s turnaround that it even pulls the Bondi crew. “The latest trends in hair and beauty are starting in places like Esstudio Galleria,” Leith-Manos says of the salon and spa in the university suburb Chippendale. Students, rockabillies and punks also amass around Newtown, a ramshackle warren of old pubs, thrift shops, LGBT bars, ethnic eateries and theaters on nearby King Street that’s regarded as Sydney’s little bohemia.

From Newtown, continue to Erskineville, home of The Imperial Hotel, where parts of the 1994 classic The Adventures of Priscilla, Queen of the Desert were filmed. In April, the place was given a new lease on life by Murat Kilic, an underground DJ and music producer who’s spent the past 20 years playing Sydney clubbers the beats they crave at his legendary Spice-themed raves, cruises and clubs. Spice Cellar ERSKNVL at The Imperial Hotel, as this latest addition to Kilic’s stable is called, plays across all genres of electronic music, sports a friendly door policy and hosts regular international DJs.

Sydney’s Inner West has also emerged as a hub for fashion and design. There are dozens of weekend markets to browse, but doyen designer Morrissey’s pick of the bunch is Rozelle flea market. “It’s a great place to find vintage glasses, scarves and old prints,” he says. And if you like the Deus Ex Machina retail spaces Oberoi and Canggu in Bali, you’re going to love The House of Simple Pleasures, the brand’s flagship store in the suburb of Camperdown on busy Parramatta Road. The House, as its known, brings together a custom motorcycle showroom, mechanic workshop, design studio, Deus boutique and a renovated-factory function space to host everything from weddings to rock concerts. Toolbox-chic… one of an endless cache of new styles born and bred in Sydney.

THE DETAILS GETTING AROUND Taxis (taxiscombined.com.au; 61-3/6334-002) in Sydney are all metered but expensive. UberX (uber.com) can be up to 30 percent cheaper. Ferry schedules can be found online (transport.nsw.gov.au).

HOTELS Inter-Continental Sydney Double Bay 33 Cross St., Double Bay; 61-2/8388-8388; ihg.com; doubles from A$314.Jonah’s 69 Bynya Rd., Whale Beach; 61-2/9974-5599; jonahs.com.au; doubles with breakfast from A$325.La Corniche B/8 Henry Lawson Ave., McMahons Point; 61-423/786-806; luxehouses.com.au; three bedrooms for A$2000 per night.QT Sydney 49 Market St., Sydney; 61-2/8262-0000; qtsydney.com.au; doubles from A$320.Watsons Bay Boutique Hotel 1 Military Rd., Watsons Bay; 61-2/9337-5444; watsonsbayhotel.com.au; doubles from A$439.

RESTAURANTS AND BARS Bang Street Food 3/410 Crown St., Surry Hills; 61-2/8354-1096; bangstreetfood.com.au; “Bang for Your Buck” sets A$55.Brown Sugar 106 Curlewis St., Bondi Beach; 61-2/9130-1566; brownsugar bondi.com.au; breakfast for two A$40.Eau-de-Vie 229 Darlinghurst Rd., Darlinghurst; 61-422/263-226; eaudevie.com.au/Sydney; cocktails for two A$24.Gastro Park 5-9 Roslyn St., Potts Point; 61-2/8068-1017; gastropark.com.au; 10-course degustation menu A$170, with wine A$290.Icebergs Dining Room & Bar 1 Notts Ave., Bondi Beach; 61-2/9365-9000; idrb.com; drinks for two A$38.Mr. Moustache Unit 3, 61/79 Hall St., Bondi Beach; 61-2/9300-8892; mr-moustache.com.au; shots from A$10.Otto Ristorante Area 8, 6 Cowper Wharf, Woolloomooloo; 61-2/9368-7488;

ottoristorante.com.au; tasting menus from A$140, with wine A$210.The Roosevelt 32 Orwell St., Potts Point; 61-2/8096-1787; theroosevelt.com.au; cocktails for two A$24, A$15 prime steaks on Wednesdays.Spice Cellar ERSKNVL 35 Erskineville Rd., Erskineville; 61-2/9223-5585; thespicecellar.com.au; tickets from A$20.Testuya’s 529 Kent St., Sydney; 61-2/ 9267-2900; tetsuyas.com; 10-course degustation A$220, with wine A$330.Vine 2 Short St., Double Bay; 61-2/9363-0010; vinebar.com.au; dinner for two plus wine from A$220.

ACTIVITIES George Street Cinemas 505-525 George St., Sydney; 61-2/9273-7300; eventcinemas.com.au; tickets from A$20. Justice & Police Museum Albert Street corner Phillip Street, Sydney; 61-2/9252-1144; sydneylivingmuseums.com.au; open weekends, admission A$10.Polo in the City Centennial Park; polointhecity.com; November 14, admission from A$138.Rozelle Flea Market 663 Darling St., Rozelle; rozellemarkets.com.au; open weekends 9 a.m. to 4 p.m.The Sydney Theatre Company Pier 4, Hickson Road, Walsh Bay; sydneytheatre.com.au; tickets from A$50.Taronga Zoo Bradley’s Head Road, Mosman; 61-2/9969-2777; taronga.org.au; zoo admission A$46, Roar & Snore camping package with dinner, breakfast and tour A$288 per person.The VIP Sydney 61-2/9697-3344; thevipaustralia.com.

STORES The House of Simple Pleasures 102-104 Parramatta Rd., Camperdown; 61-2/8594-2800; deuscustoms.com.Morrissey morrissey.com.Paspaley 2 Martin Pl., Sydney; 61-2/9232-7633; paspaley.com.Shirt Bar 7 Sussex Ln., Sydney; 61-2/ 8068-8222; shirtbar.com.au.

CLOCKWISE FROM TOP LEFT: Beauty guru Renae Leith-Manos; walking from Bondi to Bronte along the charming coast-hugging

track; A$2,000-a-night view from the living room at La Corniche penthouse apartment;

The House of Simple Pleasures; capturing sunrise over Sydney Harbour.

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