With musical genes passed down from her Cape Breton-born grandfather, Kelly started learning piano when she was 9 and earned her Teacher's A.R.C.T. from the Royal Conservatory of Music when she was 21. In Grade 8 she started playing alto saxophone in the jazz band at Semiahmoo Secondary, switching to tenor in Grade 9. She played in numerous jazz bands and combos throughout high school under the direction of David Proznick and Kevin Lee. Her saxophone influences include Dexter Gordon, Sonny Rollins, Lenny Pickett, Bob Berg, and Jr. Walker. Kelly spent her first semester after high school studying classical saxophone (oxymoron?) in college, but took a hiatus from playing saxophone when she spent 3 years living in and traveling around Australia. She joined a Celtic group in Newcastle called, Celtic Link, and took up the tin whistle and bodhran. Upon her return to Canada in 2001, Kelly joined some other Semiahmoo alumni in the soul/funk band, Southwick, playing various venues around Vancouver, including the Backstage Lounge.

It was in 2003, in her last semester of classes at Simon Fraser Unversity, that Kelly met up with Wes in Shakespeare class. They ended up in the same group for the term project and it took an inevitably musical turn. Shortly afterward, Kelly was invited to jam with the Little Brother Band and the rest is history.