Lougheed was born in Brampton, Canada West, to Irish Protestant parents, Mary Ann (Alexander) and John Lougheed. The family moved to Weston (now a community within Toronto, Ontario) when Lougheed was a child, and he attended King Street Public School (now H. J. Alexander Public School) and Weston High School (now Weston Collegiate Institute). He attended the University of Toronto and he studied law at the Osgoode Hall Law School in Toronto and was sworn in as a solicitor in 1881. In 1887 he formed a law practice with Peter McCarthy and two years later in 1889 he became a QC.