Joseph practiced law in Peterborough, Ontario from 1914 to 1930 when he was appointed to the bench as a County Couty Judge in Middlesex County and a Local Judge of the High Court Division of the Supreme Court of Ontario.

Judge Wearing was an exuberant, energetic, gregarious person, widely known in his community. He was known as well for his independent character. Prior to his appointment to the bench, he had demonstrated his loyalty to the Liberal Party chiefly through speaking at party meetings. Prior to the 1930 federal election, he knew he was being considered for a judgeship. When the Liberal government of Mackenzie King lost that election, Mr. Wearing assumed his judgeship had been lost as well. However, the appointment was confirmed by the incoming Conservative government of R. B. Bennett, apparently on the recommendation of both the outgoing and incoming Ministers of Justice.

An incident which illustrates Judge Wearing’s independence of mind occurred in 1937 when he spoke to the Downtown Toronto Kiwanis Club on the subject of “Some Things the Fathers of Confederation Did Not Anticipate.” He pointed out the the federal government had become increasingly timid about using its power under the BNA Act to disallow provincial legislation, and cited ONtario’s repudiation of certain hydroelectric power contracts and its refusal to allow redress through the courts. Judge Wearing felt that such legislation would have been disallowed in earlier times. Liberal Ontario Premier, Mitch Hepburn, called on the Liberal Prime Minister Mackenzie King, then back in office, to unseat the judge for what he considered to be unwarranted incursion into politics. Judge Wearing, however, remained on the bench. Time seems to have vindicated the judge’s constitutional analysis. The federal government’s power of disallowance was last used in 1943, and most constitutional authorities agree that it has atrophied completely.