Cowdrey was a prodigy who learned to bat as soon as he could walk thanks to his cricket-mad father. When he arrived at Tonbridge School he was placed immediately in the First XI even though he was only 13, and became the youngest cricketer to play at Lord's. He was a fine strokemaker who possessed a full array of stokes around the wicket "a masterly batsman with an excellent technique he... delighted crowds throughout the world with his style and elegance". His favourite stroke was the most pleasing – the cover drive, his son Chris Cowdrey was always asked "Why don't you caress the ball through extra cover like your father?" and replied "If I could, I would". Cowdrey also liked to experiment with new grips and unconventional strokes, to the annoyance of purists who thought his technique was already near perfect and Cowdrey himself noted that "I have not been a good player when the going is easy... unless the match provided a problem to solve, a theory to test, a hurdle to leap, a challenge worthy of battle, I have never been fully plugged in".