He was put to school at Winchester, not by his father, who had not the means, but by some wealthy patron, who is traditionally said to have been Nicholas Uvedale, lord of the manor of Wykeham and governor of Winchester Castle. The tradition further asserts that, after leaving school, he became secretary to Uvedale; and that he was secretary to the constable of Winchester Castle is stated in a written account compiled in his own time. Afterwards he is said to have been recommended by Uvedale to Edyngton, bishop of Winchester, and then by those two friends to have been made known to King Edward III. There seems to be no reason for supposing that he ever studied at Oxford, as has been affirmed by some of the later writers of his life. It is evident, indeed, that he had not had a university education, and that he never pretended to any skill in the favourite scholastic learning of his age. His strength lay in his natural genius, in his knowledge of mankind and talent for business; and probably the only art or science he had much cultivated was architecture. He is said in an ancient contemporary account to have been brought to court when he was no more than three or four and twenty, which would be about the year 1348; but the earliest office which there is the evidence of records for his having held, is that of clerk of all the king's works in his manors of Henle and Yesthampsted, his patent for which is dated 10th of May, 1356. On the 30th of October in the same year he was made surveyor of the king's works at the castle and in the park of Windsor. It is affirmed by a contemporary writer to have been at his instigation that King Edward pulled down and rebuilt great part of Windsor Castle. Wykeham had the sole superintendence of the work. Queenborough Castle, in the Isle of Sheppy, was also built under his direction.