After completing studies at St. John's Academy, Manlius, New York, where he was Head Boy in 1872, Andrews graduated from Harvard College in 1880, received his Juris Doctor degree from Columbia Law School in 1882.

[1] He returned to Syracuse, where he joined the firm Knapp, Nottingham & Andrews, working there until 1899, when he was nominated by the Republican Party to serve as the New York Supreme Court Justice in the 5th Judicial District.

In 1921, he was designated by Governor Charles S. Whitman a judge of the New York Court of Appeals, after the death of Emory A. Chase.In 1921, he was elected to a regular seat.

These included dissents in Palsgraf v. Long Island Railroad Co. and Meinhard v. Salmon, both cases in which Andrews expressed a sharply different philosophy of the responsibilities people owe to one another.

He and his wife had one child, Paul Shipman Andrews, who was the Dean of Syracuse University College of Law from 1927 to 1952.