The attachment of the homeless to the city's residual spaces is a result of a lack of choice, but in some instances, it is a preference. This thesis focuses on the latter in addressing the housing needs of those who prefer to live outdoors rather than in the institutionalized environment of emergency shelters, or even permanent housing. It explores the role of architecture in empowering independence, dignity, and security without socially engineering the homeless and changing their lifestyle. This exploration is informed by the works of architects, urban geographers, cultural critics, artists and psychologists, among them the members of the Situationist International, Bernard Tschumi, Donald MacDonald, Michael Benedikt, David Harvey, Neil Smith, and Abraham Maslow. It proposes an alternative scenario whereby those persons preferring to live outdoors may be safely, decently, and innovatively sheltered independently in some of the many residual spaces found on streets and in parks.