From Paris to Sydney and Milan to Melbourne, street style sets the scene

“My eye is just drawn to beautiful things,” Leong says. “It might be their hair or the way they are wearing the latest bag. It’s not just a matter of having the latest bag.”

Leong is part of a second wave of street style photographers, with the first round emerging alongside the rise of internet blogging culture. In 2005, former mens fashion sales associate Scott Schuman launched The Sartorialist in the US, with top-to-toe portraits of men in tailored suits, brandishing pocket handkerchiefs and fedoras that paved the way for Mad Men dressing two years before the launch of the TV series.

That year Canadian Tommy Ton started the blog Jak and Jill, which offered a more candid perspective of people outside the fashion week shows of Europe, honing in on the twist of a scarf or line of a Manolo Blahnik heel. Phil Oh completed the triumvirate, launching Street Peeper in 2006. “It’s where the fashion world and the real world intersect,” Oh says. “I love it.”

All three would go on to contribute to US Vogue’s website. When Instagram rose in prominence following its launch in 2010, their numbers swelled.

“That’s what got me interested,” says Melbourne-based street style photographer Danielle Castano. “I would follow the work of Phil Oh, as well as Adam Katz Sinding for W. I came into it from a love of fashion and taught myself the photography.”

Since taking her first street style photograph at the Melbourne Fashion Festival in 2012, Castano has gone on to work with Chanel, The Business of Fashion and Elle.

“I was in love with the way street style managed to capture the history of fashion, trends and the thoughts of designers,” Castano says. “I turned up to that fashion week with a point and shoot camera and took three photos. They were shocking, so I left.”

By the time Castano returned the next year she had taught herself more photography skills and researched other blogs. Three years later, she had left her job managing a Sportsgirl store and was capturing USVogue editor Anna Wintour and former French Vogue editor Emmanuelle Alt in Europe.

“Strangely, I don’t usually see faces,” she says. “It’s always the outfit or the accessory first. Does it feel organic? Is it something they would normally wear? In that way, making sure that the people I photograph are diverse comes naturally to me.”

Both Castano and Leong are cleaning their lenses for Australian Fashion Week, the annual industry event at Sydney’s Carriageworks starting on May 13, where designers show collections for the Resort 2025 season. They will compete for images with their peers Liz Sunshine, Myles Kalus and Giuseppe Santamaria of Men In This Town, and a new generation wielding smartphones instead of Nikon cameras.

“I really love shooting in Sydney because the community is so tight-knit,” says Leong, who broke into photography after interning in the London office of New Zealand designer Emilia Wickstead. “The photographers there are mainly females and I love the female empowerment. Honestly, in Paris I have to fight with photographers to get the shot I want.”

Castano also recalls struggling to stake her claim to a slice of sidewalk in Paris. “They’re savage,” Castano says. “It’s full-on in Europe. If everyone is photographing one person, I’ll wait for another moment.

“The only time I have ever ran and joined the fight for a shot was to get Christine Centenera [editor of Vogue Australia] outside the Chloe show… You have to face a few elbows, but that’s being a female in the photography world.”

Despite the crowds, both photographers cite Europe as home to the most inspiring street style. “Everything really does trickle down from Paris,” Leong says. “You can be at Shanghai Fashion Week and you will spot the trends filtering through from Paris. In the really cool cases, they are then matched with local styles.”

Last year, the street style at Australian Fashion Week came under fire from content creators in Europe for being more commercial than creative. “I think that Melbourne Fashion Week is definitely more commercial but that’s the nature of the event,” Castano says. “It’s more of a public event but the lines are blurring.”

“I love Australian Fashion Week street style,” Leong says. “Sometimes in Paris, people go all out and then it can be too much. Everything in Sydney seems to be laid back. There’s something about the style that you guys bring that is so different. I love seeing people who blend the top European labels with local designers. There’s plenty of playful layering with bold colours.”

That joy is tempered by the economic challenges facing the fashion industry, which is trickling down to street style photographers. Both Leong and Castano have noticed an increase in demands from media and fashion clients and a decrease in budgets.

“It’s increasingly becoming a pay-for-play space,” says Castano, who has noticed a rise in influencers hiring their own photographers and video teams to support their clients and supply images to publications for free.

“There is increasingly less money for photographers, which is frustrating as the galleries we supply are some of the most popular products in the media landscape… There are so many more photographers out there, which is great, except when they work for free. It devalues what we do.”

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While being an influencer can become a full-time career, at the other end of the lens side hustles are often required to stay on the streets. Castano consults to fashion brands on content strategies and works on more traditional photography assignments. In Singapore, Leong works part-time for her family’s construction business.

“Obviously, I would love to be doing this all the time,” Leong says. “But it keeps my senses sharp. Going from construction to fashion keeps your viewpoint fresh.”

With financial incentives dwindling, the motivation for both women is the same thing that separates them from other photographers. “You can’t do this job without being 100 per cent in love with fashion,” says Castano.

“That doesn’t mean you have to know who Emmanuelle Alt is or Anna della Russo [the flamboyant editor-at-large for Vogue Japan] but it helps. It’s knowing how fabric sits against fabric. The crush of a leather bag against a silk shirt. That love comes through in the photographs.”

There are also new frontiers to explore, with Sydney, Milan and Paris becoming crowded. “Last year I went to Kazakhstan and, after Sydney, I am going to fashion week in Uzbekistan,” Leong says.

“I am looking forward to seeing the way people in Central Asia interpret the European trends. In fashion there is always a new way of looking at the world.”

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