Wheare was educated at the Dragon School and Magdalen College School in Oxford. He then went on to King's College Cambridge (gaining an exhibition, studying History, and singing in the College Choir) and Christ Church, Oxford (studying Education for a Dip.Ed. and acting as a lay clerk in the Christ Church Cathedral Choir).
During his career as a teacher, he has been a Housemaster at Shrewsbury School and Assistant Master at Eton College. From 1983 to 2005, he was Head of Bryanston School in Dorset. The Tom Wheare Music School at Bryanston, designed by Hopkins Architects, was opened in September 2014.
Wheare was an active member of the Headmasters' and Headmistresses' Conference (HMC), serving as Treasurer from 1993 to 1999, and Chairman in 2000. He has been a governor of a number of schools over the years, including Blackheath High School, the Dragon School, Exeter School, and Port Regis School. He is Deputy Chairman of the Girls' Day School Trust and has been a member of the Executive Committee of the Association of Governing Bodies of Independent Schools (AGBIS).
- Tom Wheare, Girls' Day School Trust.
- Tom Wheare: ZoomInfo Business People Information, ZoomInfo.
- Buffalo Bulletin, Autumn 2003.
- About Bryanston — History, Bryanston School.
- Holdsworth, Angela (ed.), Bryanston Reflections: Et nova et vetera. London: Third Millennium Publishing, 2005. ISBN 1-903942-38-1.
- "The Tom Wheare Music School". Retrieved 22 March 2015.
- "Hopkins completes another Bryanston School building". Architects Journal 2 March 2015. Retrieved 22 March 2015.
- "School opens new state-of-the-art music school". Dorset Echo. 18 Sep 2014. Retrieved 22 March 2015.
- "The new Tom Wheare Music School". Retrieved 22 March 2015.
- "GDST Trustees". Retrieved 22 March 2015.
- Wheare, T.D. (ed.), Which School? 2008, John Catt Educational Ltd, 2007. ISBN 978-1-904724-43-8.
- Wheare, T.D. (ed.), Which School? 2009, John Catt Educational Ltd, 2008.
- "Joan Wheare: Oxford's 'urban guerrilla'". Oxford Mail. Retrieved 22 March 2015.
|Head of Bryanston School