Shape knowledge, a key aspect of school readiness, is part of early mathematical learning. Variations in how children are exposed to shapes may affect the pace of their learning and the nature of their shape knowledge. Building on evidence suggesting that child-centered, playful learning programs facilitate learning more than other methods, 4- to 5-year-old children (N = 70) were taught the properties of four geometric shapes using guided play, free play, or didactic instruction. Results revealed that children taught shapes in the guided play condition showed improved shape knowledge compared to the other groups, an effect that was still evident after 1 week. Findings suggest that scaffolding techniques that heighten engagement, direct exploration, and facilitate “sense-making,” such as guided play, undergird shape learning.