An important part of being middle-class has been based on having access to exclusive educational and cultural activities. Studies have revealed that the idea of a good school is conflated with its class and ethnic intake where parents tend to avoid subordinated groups. Working-class children and especially black boys are positioned as valueless and are not viewed as sources of multicultural capital. This chapter argues that middle-classness must be understood in relation to other sociocultural categories. It is strongly associated with whiteness, resulting in difficulties for ethnic-minority middle-classes to ‘feel’ middle-class or to even be recognized as middle-class. The interrelation between family habitus and field was empirically explored through many kinds of data collection. In addition to conducting interviews with families, the chapter explores media discussion about school choice, the desegregation plan and other educational issues in conjunction with conducting observations and interviews with school authorities in Osborne school.