[4] As a teenager, she moved to the Lower East Side and attended the City-As-School High School in Manhattan, but dropped out at the age of sixteen and began taking photographs using her mother's camera.

[5][3] She has spent most of her adult life living in New York City, whose built environment has been the subject matter of much of her work (e.g. sidewalks, storefronts, apartment buildings, chain-link fencing, graffiti, and boarded-up windows.

From her earliest aerial photographs to her images of museum displays, anatomical models, and fashion shows, much of Leonard's work reflects on the framing, classifying, and ordering of vision.

[13] During the mid-1990s Leonard spent two years living and working in Eagle, Alaska, an experience that influenced much of her later artwork, which often foregrounds relationships between humans and the natural world.

[14][15][16] While in Alaska, she worked on a farm, a commercial fishing boat, and for the National Park Service, and went on to create a photographic series, Hunting, based on her experiences with subsistence economies.

[22] Holland Cotter described an experience of the work in The New York Times in 2009: "In her straight-ahead photographs of storefronts, an arrangement of shoes or shrink-wrapped furniture becomes a vanitas still life.

Over several photographs, we sense that an unnamed neighborhood — Ms. Leonard expanded her field work to include East Harlem, Bedford-Stuyvesant and Crown Heights — is packing up to leave.

Many of the cut-rate goods sold in the Lower East Side shops originated in urban sweatshops in China and Pakistan and are eventually passed on as surplus to other poor cities in Africa and Central America.

In the wraparound grid of pictures in Analogue we follow recycled clothes from Brooklyn to the city of Kampala in Uganda, where they are sold as new in stores like the Money Is Life House of Garments.

[26] Other exhibitions such as Serialities at Hauser & Wirth, Observation Point Archived 2014-01-02 at the Wayback Machine, Camden Arts Centre, London (2012), an installation at the Chinati Foundation, Marfa, Texas (2013-2014) and the 2014 Whitney Biennial, for which Leonard won the Bucksbaum Award with her work "945 Madison Avenue".