Purpose: This study examined the head orientation of young children in naturalistic settings and the acoustics of their everyday environments for quantifying the potential effects of directionality. Method: Twenty-seven children (11 with normal hearing, 16 with impaired hearing) between 11 and 78 months of age were video recorded in naturalistic settings for analyses of head orientation. Reports on daily activities were obtained from caregivers. The effect of directionality in different environments was quantified by measuring the Speech Transmission Index (STI; H. J. M. Steeneken & T. Houtgast, 1980). Results: Averaged across 4 scenarios, children looked in the direction of a talker for 40% of the time when speech was present. Head orientation was not affected by age or hearing status. The STI measurements revealed a directional advantage of 3 dB when a child looked at a talker but a deficit of 2.8 dB when the talker was sideways or behind the child. The overall directional effect in real life was between -0.4 and 0.2 dB. Conclusions: The findings suggest that directional microphones in personal hearing devices for young children are not detrimental and have much potential for benefits in real life. The benefits may be enhanced by fitting directionality early and by counseling caregivers on ways to maximize benefits in everyday situations.