Some of the great advantages (and challenges) of outdoor photoshoots over studio work are the creative possibilities. Not just in pose and expression, but in how you choose and utilize the environment to complement or contrast with your subject. Not just physical objects and backdrops, but the colors, light and textures can all contribute to the mood or story of a shot.
I usually plan a few specific shots in advance of a portrait or model shoot, then improvise on the day to allow for creativity and freedom through the shoot itself. Even if I know the locations well or have scouted them out in advance, I'll often arrive early for a shoot just to check how the light is that day and whether anything has changed from when I was there last. If you want a certain mood or light, or to complement your subject in certain way, then choosing a suitable location becomes a key decision in the planning process.
For local shoots in New York, here are a few of my favorite locations at the moment.
Maybe the most obvious location for portraits, there are plenty of interesting rocks, lakes and other features in the southern end of the park, or head further north to find quieter spots away from other people. Belvedere Castle and Bethesda Terrace are both good spots although can get crowded.
Another way to escape from the busy streets, although the Highline can also still get pretty crowded in places, especially in summer and at weekends. It does offer some nice backdrops though, with the park itself as well as views down over the streets and some good nearby locations in the Meatpacking District.
For less visitors and more locals, the east village is maybe my favorite Manhattan location. From tattoo parlors to vintage record shops and trendy coffee shops, there is plenty of street art too. East of Tomkins Square Park there is also a variety of small, privately maintained gardens that are open to the public.
Battery Park is nice and you could combine it with a trip on the Staten Island ferry. Chinatown is great if you want that particular look and I'm hoping to try a portrait shoot there after dark one evening. I particularly like though the area the piers and Two Bridges with views out over Brooklyn.
I'm not sure I've ever been to Dumbo (Down Under the Manhattan Bridge Overpass) without seeing at least one other photoshoot going on. It's a classic location, especially around Jane's Carousel and the sunset views of Manhattan heading west around Brooklyn Bridge Park. The streets away from the water are worth exploring too with re-purposed warehouses and a mix of older industry alongside artisan startups.
Hip and trendy, the artists might be long gone to find cheaper neighborhoods and the thift stores are now priced liked fashion boutiques, but there's a still an unmistakable charm about Williamsburg even if some of the authenticity has been lost. Bedford Avenue is a good street to work out from and I particularly like the little Grand Ferry Park and the streets nearby.
Ahh, Coney. Crazy on a summer weekend but full of interesting characters, it can feel like a ghost town near the water in the middle of winter. I love being by the ocean anyway, and I like the quirky, slightly run-down feel to the place. The boardwalk, pier and old roller coasters are all good backdrops, although sometimes I just like enjoying the beach itself.