Cultural awareness, when applied to Intelligent Learning Environments (ILEs), contours the overall appearance, behaviour, and content used in these systems through the use of culturally-relevant student data and information. In most cases, these adaptations are system-initiated with little to no consideration given to student-initiated control over the extent of culturalawareness being used. This paper examines some of the issues relevant to these challenges through the development of the ICON (Instructional Cultural cONtextualisation) system. The paper explores computational approaches for modelling the diversity of students within subcultures, and the necessary semantic formalisms for representing and reasoning about cultural backgrounds at an appropriate level of granularity for ILEs. The paper investigates how student-initiated control of dynamic cultural adaptation of educational content can be achieved in ILEs, and examines the effects of cultural variations of language formality and contextualisation on student preferences for different types of educational content. Evaluations revealed preliminary insight into quantifiable thresholds at which student perception for specific types of culturally-contextualised content vary. The findings further support the notion put forth in the paper that student-initiated control of cultural contextualisation should be featured in ILEs aiming to cater for diverse groups of students.