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How to Get Shot for Street Style, According to a Professional Photographer

If you're trying to get photographed outside the shows, start here.
On the street at Mercedes-Benz Fashion Week Australia. Photo: Lee Oliveira/Fashionista

On the street at Mercedes-Benz Fashion Week Australia. Photo: Lee Oliveira/Fashionista

It's a beautiful, mild morning in Sydney and I'm at Carriageworks, the site of Mercedes-Benz Fashion Week Australia, standing next to a rather nondescript gray wall — too close to it, actually, according to street style photographer Lee Oliveira.

"You don't want to be like a wallpaper, in a way; you want to give sort of a depth in the picture, and give a good composition," he explains to me over a coffee a bit later. "Like you're matching all your outfits, from your ready-to-wear to accessories, as a photographer, I also like to match my composition."

I've asked Oliveira about getting shot for street style, not just because he's my friend and I like to talk to him, but also because he's a veteran photographer, having worked with everyone from The New York Times to, well, us here at Fashionista. He knows so much about his side of the industry that he's even worked with influencers, helping to style them and coaching them on to the next level of their careers. 

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All this to say that Oliveira knows what makes for an interesting shot on the sidewalk. As for me, you could argue that I've always found the street-style game more than a little intimidating, which is why I've asked Oliveira to give me a few tips of my own while I'm in Sydney. The conditions seemed perfect, thanks to the early autumn timing of the shows — we're talking blue skies and 70-degree days — and a more relaxed schedule than one of the major fashion weeks. 

So back to that gray wall: Oliveira sets up the shot and asks me to walk towards the camera. It feels stilted and awkward, and I can't resist adding in a goofy jump. That's okay, according to Oliveira, who has me do it again so he can properly capture it. "Just be yourself!" he says. 

That part seems easy enough, but what about the rest? With fashion month on the horizon, I thought I'd share more of Oliveira's tips for getting shot for street style, if that's your thing. Read on to learn his keys for maximizing your time on the sidewalks this season.

On the street at Mercedes-Benz Fashion Week Australia. Photo: Lee Oliveira/Fashionista

On the street at Mercedes-Benz Fashion Week Australia. Photo: Lee Oliveira/Fashionista

Think ahead

It may seem like a no-brainer, but take a look at your schedule and plan your outfits accordingly. It's been a trend for a long time, but if you're traveling with a friend or co-worker, matching outfits can make for a guaranteed snap. And take advantage of your environment; try and scope out the show venues in advance, if you're not familiar. 

"Some people are very smart — they know the outfits in terms of the location, so it matches the background," he says. "For example if you're going to the Milk Studios, which is dark in winter, you always bring a color." 

Remember that gray wall? The pink of my dress provided a great pop, which is what made it work. (Totally unintentional, but now I know!) If you're going to be outside, try a fun pattern; bright colors will work well in the dull days of winter; Oliveira notes that there are editors who know precisely how to work with the unique light of Parisian days. And it doesn't even have to be sunny; in fact, gray conditions can make for the best photos.

Don't ask to be photographed

Remember, street style photographers are there to work, either for themselves or for someone providing their paycheck — and unless that someone is you, don't approach and ask to have your photo taken. They aren't there to be your personal photographer.

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"It's very uncomfortable, because sometimes it's like, I don't know what to say, or I might not like your outfit or I've seen it before, or I'm not expecting you, I'm waiting for somebody else," Oliveira explains. "I don't do that to editors or directors; I don't stop them and say, 'Can you write about me please?'"

On the flip side, though, Oliveira notes that it can be smart to befriend the photographers if you want to be shot more; many are more likely to notice familiar and friendly faces in the crowd.

On the street at Mercedes-Benz Fashion Week Australia. Photo: Lee Oliveira/Fashionista

On the street at Mercedes-Benz Fashion Week Australia. Photo: Lee Oliveira/Fashionista

Move strategically through the crowd

If you're like me, your inclination is probably to pick through the throngs of people outside as quickly as possible. But if you're trying to photographed, you'll have to think of things a little bit differently — with a photographer's eye. Carry yourself with confidence and pick a route past an interesting wall, for example, or through a gap in a crowd where the lighting is good (which, by the way, is not in direct sunlight), so that you're providing an interesting set up for photographers.

"That's what makes a good picture interesting, because again, there's a lot of street photographers out there, and we are shooting exactly the same person, the same bag, same shoes," Oliveira explains. "To me, it's like, how can I make it different? How can I make the picture stand out slightly different to the others?"

Photographers move around the venue as well, which means if you have your hopes set for a certain outlet or photographer, remember that you have two chances to find them. "If you didn't get me in the entrance, you might get me in the exit," he explains.

Just don't stand around and pretend to be on your phone. Photographers know that move and many don't like the look of a clearly staged shot.

On the street at Mercedes-Benz Fashion Week Australia. Photo: Lee Oliveira/Fashionista

On the street at Mercedes-Benz Fashion Week Australia. Photo: Lee Oliveira/Fashionista

Don't take it personal

Easier said than done? Maybe! But Oliveira notes that preferences vary not just from photographer to photographer, but outlet to outlet and even day to day. "Some people have a different taste in fashion — some people like very loud fashion to photograph, some people like print-on-print to photograph, some people are very plain or just black," he explains. Just as much as style varies, sometimes the conditions aren't good for taking photos; maybe the lighting has gone away, or it's too crowded to get a clear shot. And know that you won't get photographed every single time by the same photographers. 

"I actually had some editors, which I felt was quite fascinating, come and approach and ask you why you don't shoot their looks in some days," he says. "Some of them change outfits three to four times a day. I don't work for, for example, Getty, which is a platform that needs so much content per hour; I'm just feeding a publication or even just my channel, so I don't need looks every day. I'm not doing a style profile on anyone."

At the end of the day, your personal style is just that: Personal. If you're feeling yourself, photos are just a bonus. 

See the rest of Lee Oliveira's shots from Mercedes-Benz Fashion Week Sydney in the gallery below:

IMG provided my travel and accommodations for Mercedes-Benz Fashion Week Australia.

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