The Trews were formed in Antigonish, Nova Scotia in 1998. Originally named One I'd Trouser, and then shortened to Trouser. They finally settled on The Trews. Brothers Colin and John-Angus MacDonald recruited their long time friend Jack Syperek on bass. For the role of drums their cousin Sean Dalton was selected.

The bands big break came when then won a competition held by Ontario rock radio station CHTZ-FM. The prize was a recording contract with Sony BMG Canada. In 2003 they released their début CD House of Ill Fame which was met with fairly positive reviews. It spawned the hits "Every Inambition", "Not Ready to Go", "Tired of Waiting" and "Confessions". "Not Ready to Go" was an instantaneous hit, winning the number one spot on Canadian rock radio. It was also the most played song of 2004 within the rock radio format. In 2004 The Trews were nomminated for the New Group of the Year category at the Juno Awards.

Their next album came in 2005 released on Epic Records. Titled Den of Thieves. The album spawned the singles, "So She's Leaving", "Yearning" and "Poor Ol' Broken Hearted Me".

No Time for Later was their third album, released in 2008 on Bumstead Records. The singles include "Hold Me in Your Arms", "Paranoid Freak", "Man of Two Minds" and "Can't Stop Laughing". The album had moderate reviews, but managed to début at number 4 on the Canadian Albums Chart.