How Auckland’s High Street regained its charm

The old-world attractions of Auckland’s High Street have been transformed with bespoke tailors, hip guesthouses and craft beer bars.

The old-world attractions of Auckland’s High Street have been transformed with bespoke tailors, hip guesthouses and craft beer bars.

Once a hotbed of the debauched and deprived, Auckland’s High Street is now an intimate, curated community attracting the city’s best talent – high-end tailors share the street with cafes, boutique hotels and creative agencies.  

By one count, just a handful of new buildings have been built on High Street – the narrow lane that runs behind downtown Auckland’s main street – since World War II. Even as the city has grown around it, skyscrapers marching down towards the harbour, High Street and its surrounding lanes have retained an intimacy that belies the fact that this is the heart of New Zealand’s largest city. The buildings are small – just four and five storeys with big windows – and cars are secondary to pedestrians.

Once the home of a nascent New Zealand fashion scene including the iconic Zambesi, the area’s fortunes have waxed and waned over the years. But in recent years, High Street has undergone yet another of its mutations, emerging revitalised as the city’s pre-eminent menswear district and home of its hippest small hotel. 

Downtown Auckland was developed piecemeal by speculators and developers in the first couple of decades after its founding in 1841: the parallel High Street and O’Connell Street began life as service lanes for the more prestigious Shortland Street; the pedestrian Vulcan Lane that connects them, meanwhile, was known as Vultures Lane, on account of the harlots, gamblers and journalists who drank in the pubs there. Their fortunes declined further in the 1860s when a fire destroyed much of the area: the buildings, this time, were rebuilt with their frontages facing onto Queen Street.

Nothing much happened until the 1970s when New Zealand fashion designers began to move in, including labels such as Zambesi, World and Kate Sylvester. The area’s most recent transformation began with investment by the local council into the streetscapes, which is ongoing, and the multimillion-dollar refurbishment of historic Hotel DeBrett in 2007. Previous owners Michelle Deery and her husband John Courtney spent two years renovating the small hotel that is noted for its mid-century furniture, art deco bar and restaurant in a light-filled atrium. 

The hotel takes up almost a whole block. It has a number of ground-floor shops and as tenancies have changed, Deery has hand-picked new operators. “It was crucial that we curated the neighbourhood,” she says. “That we didn’t just take anyone in to pay the rent. It was about community and getting the right mix.” 

Boutique tailor Crane Brothers moved into one of those stores when the lower end of the street wasn’t that fashionable. “It had always been such a core part of the cultural life of Auckland,” says creative director Murray Crane, who started working in the area in 1990. 

On neighbouring Shortland Street, you’ll find the offices of most major Auckland law firms, along with venture capitalists and accounting firms. Their people drink coffee at Giles Luncheonette and have lunch at Pilkingtons, an airy new restaurant in a pavilion designed by local architectural hero Nat Cheshire. Other retailers have joined Crane Brothers – New Zealand menswear retailer Barkers is across the road, while business shirt retailer Three Wise Men and shirtmaker Nicholas Jermyn are next door.

Paul Bartolo, a Londoner, opened Bespoke Barbers on O’Connell Street early in 2015. It’s a traditionally masculine space: green walls, dark timber, classic cuts, a wet shave if you want. “I watch people and their body language changes,” says Paul Bartolo of his attraction to the area. “I watch them come from busy Queen Street and they sit down here and have a cup of coffee.” Bartolo says he expected most of his clients to be suits but in the heritage spaces above High Street there are more designers, architects and boutique ad agencies now. “The really beautiful thing,” he says, “is that we’re getting a lot of creatives back to the city now.” 

They drink coffee in Chuffed – tucked down a long hallway with one of the city’s more delightful terraces – and the new flagship café from boutique roaster Eighthirty, which has a striking white-and-red fitout, located down the end of a mid-century arcade. And they drink, not surprisingly, on Vulcan Lane, where two of those fantastic old pubs have found new life as craft beer bars. At Urchin and Amber and Vultures’ Lane – places with multiple taps and an ever-changing line-up – you can get a beer and marvel that this is where the depraved and deprived of the city once roamed.

How to Get There
Auckland Airport is the main gateway to New Zealand. High Street, meanwhile, is a short walk from major bus, train and ferry networks. 

Best Time to Visit
Between February and April, Auckland basks in settled sunshine and long, fine days – the city’s residents lap it up at night markets and music festivals, or head to the beach.

What’s Nearby
It’s an easy walk to Britomart, a stylish waterside shopping and dining precinct. Take a 35-minute ferry ride to Waiheke Island and have lunch at a vineyard or head southeast of Auckland to Clevedon for a pretty countryside of rolling farmland and sheltered coastline with small sandy bays. Time it for Sunday, when some of the city’s finest artisan producers are at the Clevedon Valley Farmers’ Market.