Shrewsbury School Headmaster Leo wins prestigious Tatler Schools Award

The prestigious accolade, which is voted for by parents and the wider school community, recognises Mr Winkley’s exceptional leadership, forward-thinking vision, and deep commitment to a 'whole person' approach to education.

The news was met with widespread congratulations from within the school and the broader education sector, with many lauding his combination of modern innovation and deep-seated integrity.

A Leader of Integrity and Vision

Since his appointment in 2018, Mr Winkley has presided over a period of significant growth and recognition for Shrewsbury School, which is celebrating its 473rd year. Under his stewardship, the school has successfully preserved its unique heritage while continually championing innovation, leading to it being named Independent School of the Year in 2020.

Quotes from the school community underline the Headmaster's influential style. Meg H, Shrewsbury’s Head of School, praised the "combination of compassion with direction that has made Mr Winkley’s leadership so special," while fellow Head of School, George R, noted his approachability as "a listening ear – both receptive to and actively interested in the concerns and recommendations of every pupil."

Chair of Governors, James Pitt, emphasised the transformative nature of Mr Winkley’s tenure: "His commitment to Shrewsbury’s distinctive model of whole person education... whilst still having 'serious fun' — has been transformative for our school community."

Whole Person Education and Community Focus

The Headmaster's ethos is vividly expressed in the school’s highly praised Partnership and Community Engagement programme, which was awarded the rare accolade of a ‘Significant Strength’ by the Independent Schools Inspectorate.

Drawing inspiration from former pupil Charles Darwin, Mr Winkley often champions the idea of 'survival of the kindest,' believing that a strong sense of social responsibility and caring for others should be central to the learning experience. Dr Joe Spence, CEO of The School Partnerships Alliance, affirmed this, calling Mr Winkley "one of the great Heads of his generation... savvy and selfless and a great supporter of all that matters in education, in and beyond the classroom."

Beyond the main campus, Mr Winkley has also guided the growth of the Shrewsbury Family of Schools to eight institutions worldwide, with the recent addition of Terra Nova in Cheshire, ensuring the Shrewsbury ethos has a positive global impact.

"This Award is All About Shrewsbury"

Responding to the win, Mr Winkley expressed deep humility, stating: “Receiving the Tatler Schools Guide Best Head of a Public School 2026 Award is deeply humbling... This award is all about Shrewsbury. Any leader is only as good as the people around them.”

He stressed that the national recognition is a reflection of the entire community, adding: “This award belongs not to one person, but to every member of the Salopian community... It is a tremendous privilege to follow in the footsteps of my 27 predecessors as Heads of Shrewsbury.”

The Tatler Award joins a growing list of commendations for Shrewsbury since 2020, including being a finalist for Community Engagement in the Talk Education Awards 2025 and an Edtech 50 Award winner for Innovation in AI and Digital Learning.

Senior Deputy Head, Mr Kevin Brennan, concluded that the award is a "richly deserved honour" reflecting the voices of parents and the community, confirming that Mr Winkley's principled leadership ensures the school will "continue to thrive and flourish as a place where every pupil can reach their full potential.”