Leo Winkley was born into a teaching family and grew up as a staff child at Cranleigh School in Surrey. When his father was appointed Second Master of Winchester College, Leo and his brother remained at Cranleigh School as boarders. After school, Leo studied Theology at the University of Oxford (Lady Margaret Hall) where he played hockey and was involved in drama productions. After university, he qualified as a teacher of English as a Foreign Language and lived in Paris and the Loire Valley for two years, teaching and helping to restore a run-down château.
Leo then began his teaching career as Head of Religious Studies at Ardingly College (1994-99) where he also looked after a Lower Sixth boarding house. From there, he moved to The Cheltenham Ladies’ College as Head of Religious Studies (1999-2004) where the subject became the most popular A Level choice. In 2004, he was appointed Deputy Head of Bedales School (2004-10) where he was responsible for boarding and pastoral care. He then spent eight years as Head Master of St Peter’s School in York. The school was rated ‘excellent’ in all areas by the Independent Schools Inspectorate in 2017.
A passionate advocate of boarding, Leo was Chairman of the Boarding Schools’ Association (2016-17) which represents over 500 state and independent boarding schools. He believes strongly in community engagement and partnership work, chairing the City of York Independent State Schools Partnership (2017-18) and sitting on the Independent Schools’ Council expert group ‘Schools Together’.
Leo is married to Jules, a medical oncologist. They have two daughters and a son, who share the family house with two cats and two pet rats. The Winkleys love spending time outdoors together enjoying the beautiful Shropshire countryside. Leo is also a keen runner, having completed a number of marathons in what he describes as "solid and unremarkable times". He enjoys a broad range of sports as well as gentler pursuits such as watercolour painting. He supports Arsenal Football Club (and more recently Shrewsbury Town) and confesses to having an obsessional love of anteaters.
On the first staff INSET day of the Michaelmas Term, and to mark the start of his tenure as the 28th Headmaster at Shrewsbury School and celebrate the beginning of the new academic year, Leo Winkley gathered together all the teaching and support staff for a 'Shrewsbury School Family Photo' and meal.