Shrewsbury School Headmaster Leo Winkley wins National Award

• “Leo is one of the great Heads of his generation.” Dr Joe Spence, Chief Executive Officer of The School Partnerships Alliance
• “He is an intellectual person who is absolutely devoted to his job - he will always do the right thing, with great integrity.” Shrewsbury Parent 2025
• “It is the combination of compassion with direction that has made Mr Winkley’s leadership so special.” Meg H, Shrewsbury’s Head of School
• “A listening ear - both receptive to and actively interested in the concerns and recommendations of every pupil.” George R, Shrewsbury’s Head of School
• “He is a big-picture thinker who balances tradition with a modern, forward-looking approach. His dedication to fostering a sense of ‘serious fun’ is unparalleled.” Shrewsbury Parent, 2025

Shrewsbury School is proud to announce that its Headmaster, Leo Winkley, has been named Best Head of a Public School in the Tatler Schools Awards 2026. This prestigious accolade, voted for by parents and the wider school community, recognises Mr Winkley’s inspirational leadership, vision, and unwavering commitment to whole person education.

Since his appointment in 2018, Shrewsbury has flourished under Mr Winkley’s leadership, preserving its unique 473-year heritage and traditions while continuing to innovate and champion a whole person approach to education. In 2020, Shrewsbury was named Independent School of the Year.

Shrewsbury’s Partnership and Community Engagement programme, recognised by the Independent Schools Inspectorate with the rare accolade of a ‘Significant Strength’, is a clear expression of this ethos in action. Inspired by Old Salopian Charles Darwin, the Headmaster often speaks of ‘survival of the kindest,’ believing that every pupil and member of staff benefit from partnerships. At Shrewsbury, caring for others, building connections and developing a strong sense of social responsibility are placed at the heart of learning beyond the classroom.

Mr Winkley’s clarity of vision has also guided the measured growth of the Shrewsbury Family of Schools to eight schools. From Hong Kong to Cambodia, and most recently with the addition of Terra Nova in Cheshire, the Shrewsbury ethos continues to make a positive impact on education worldwide.

Shrewsbury’s Headmaster, Leo Winkley said:

“Receiving the Tatler Schools Guide Best Head of a Public School 2026 Award is deeply humbling. As I said at the awards ceremony, this award is all about Shrewsbury. Any leader is only as good as the people around them.

“This national recognition is a reflection of the special nature of our school community. I hope it also reflects positively on the town of Shrewsbury with which we share not just a name but a deep connection. 

“In our 473rd year, Shrewsbury School remains a very special place. In my eighth year as Headmaster, my time is just a moment in the long history. It is an honour to be the current custodian of the Salopian community. It is a tremendous privilege to follow in the footsteps of my 27 predecessors as Heads of Shrewsbury. It is my job to look after everything that makes Shrewsbury School distinctive. 

“This award belongs not to one person, but to every member of the Salopian community across the UK and around the globe. To each pupil who makes every minute at Shrewsbury matter, to every family who supports us, to every teacher whose dedication inspires and to the support staff whose tireless work keeps our school flourishing, to our Governing Body and all our alumni and supporters around the world. Floreat Salopia!”

Chair of Governors for Shrewsbury School, James Pitt said:

“The Governors of Shrewsbury School are delighted to see Mr. Leo Winkley's inspiring leadership and unwavering dedication recognised with this prestigious accolade from Tatler.

“His commitment to Shrewsbury’s distinctive model of whole person education - Floreat, which offers deep learning in a challenging yet kind environment, whilst still having “serious fun” - has been transformative for our school community.

“This award is a testament to the culture of integrity, compassion, and innovation he has cultivated among pupils and staff alike.”

Shrewsbury’s Head of School, Meg H (M, UVI) said:

“Mr Winkley’s collaboration with pupils and his drive to ensure our voices inform school policies have facilitated meaningful change and created a community of people who feel valued. It is this combination of compassion with direction that has made Mr Winkley’s leadership so special. Congratulations Mr Winkley!”

Shrewsbury’s Head of School, George R (SH, UVI) said:

“Mr Winkley is a headmaster who feels more like a colleague than a teacher for us as pupils. Despite his strong authority and respect from the pupil body, he always remains approachable and friendly - a listening ear both receptive to and actively interested in the concerns and recommendations of every pupil.

“He is always looking for ways to improve the school community while exemplifying its core values from the top down, and it's truly an honour to lead the school under his guidance and work so closely with him.”

During Mr Winkley’s leadership, since 2020, Shrewsbury has received a series of prestigious awards and commendations: finalist in the Talk Education Awards 2025 for Community Engagement; shortlisted for Boarding School of the Year at the Independent Schools of the Year Awards; winner of the Edtech 50 Award for Innovation in AI and Digital Learning; ranked among the Top 25 UK senior schools in the Spear’s Index; recipient of the Oppidan Gold Mentoring Award; and praised in the ISI Report 2024 for its Partnership and Community Engagement as a “significant strength.”

Senior Deputy Head at Shrewsbury School, Mr Kevin Brennan said:

“We are delighted that our Headmaster, Mr Leo Winkley, has been awarded Best Head of a Public School in the Tatler Schools Guide 2026 Awards — a richly deserved honour made all the more special because it reflects the voices of parents and our wider school community.

“Entering his eighth year as Headmaster at Shrewsbury, Mr Winkley continues to drive our commitment to a whole person education — nurturing intellectual curiosity, personal integrity, and a spirit of service that equips our pupils for life beyond our gates.

"In challenging times for the UK independent sector, we are deeply grateful for the clarity of vision, wise stewardship, and principled leadership he brings to our school — qualities that ensure Shrewsbury will continue to thrive and flourish as a place where every pupil can reach their full potential.”

Dr Joe Spence, Chief Executive Officer of The School Partnerships Alliance said:

“Congratulations to Leo Winkley on the award of Tatler ‘Best Head of a Public School’ 2026. That’s a richly deserved accolade. Leo is one of the great Heads of his generation. He’s savvy and selfless and a great supporter of all that matters in education, in and beyond the classroom; in and beyond Shrewsbury. 

“That Leo has been recognised in this way will please everyone in the independent school community, but it will also delight those of us who know the work he does - quietly and effectively - to support state schools and maintained-independent school partnerships.”

Head of the Shrewsbury School Parents Association, Anne Barrett said:

“Any school, particularly a boarding school, is an extension of the family; we are so lucky to have Leo as the head of our extended family.

“He sets a tone of respect, endeavour, community and inclusion for all our children - and it’s so lovely to watch them becoming kind, thoughtful and committed young adults under his leadership.”

Robin Fletcher, CEO, Boarding School Association said:

"Leo Winkley's recognition as Public School Head of the Year in the Tatler awards is well deserved. Leo is a true champion of boarding education and was a distinguished Chair of the BSA in 2017, a position his father Stephen Winkley also held."

Vicki Parker, Chief Executive Officer of Shrewsbury House (‘The Shewsy’), said:

“I am absolutely delighted that Leo has been recognised for his outstanding leadership of Shrewsbury School.

“Since 2021 Leo has been Chair of the Board of Shrewsbury House, a charity set up in inner city Liverpool by teachers from Shrewsbury School in 1903.

“As Chair of our Board, Leo embodies visionary leadership, combining strategic insight with a deep commitment to creating opportunities for disadvantaged children in one of the poorest wards in Europe. This recognition is a fitting testament to his dedication to improving young people’s lives.”

Chairman of The Sanata Charitable Trust (Restart Africa), Chris Conway said:

“Restart Africa is a home for abandoned street children, many of whom have been the victims of appalling abuse. The aim is to look after these children, put them through education, and ultimately enable them to obtain employment and thus survive and thrive within Kenyan society. 

“Shrewsbury’s support has been transformative for Restart Africa – not just in fundraising money to support the charity, but in supporting their education, building friendships and raising aspirations for our children. The Headmaster’s belief in our mission, and his leadership in putting children’s needs first, have been invaluable. We are immensely grateful and delighted to see him honoured with this national award.”

Karen Williams, Project Lead, Foodbank PLUS, said:

“Working in partnership with Leo Winkley and Shrewsbury School for some years has clearly demonstrated the shared values of community and value of each person within the wider community.

“Leo has epitomised this value of community with his personal welcome and wanting to work together for the long term for the benefit of the whole community.

“From weekly student volunteering to the annual Christmas Fair, the partnership is not primarily about fundraising. The culture I experience with my interactions with Leo reflect the commitment to truth, ambition for everyone to achieve their personal potential and the desire for a community to flourish.”

Headmaster Leo Winkley, Biography:

Leo Winkley grew up in a teaching family at a boarding school in Surrey, where his father was a Headmaster. After studying Theology at Oxford (Lady Margaret Hall) – where he played hockey and acted in drama productions – he taught English in France before starting his teaching career as Head of Religious Studies at Ardingly College. He went on to lead the department at The Cheltenham Ladies’ College, became Deputy Head of Bedales, and then spent eight years as Headmaster of St Peter’s School, York, rated ‘excellent’ in all areas by the ISI. In September 2018, he was appointed the 28th Headmaster of Shrewsbury School.

A passionate advocate of boarding, Leo chaired the Boarding Schools’ Association (2016–17) and has helped shape national conversations around partnership and community engagement. He has a Master’s in Education, a Postgraduate Certificate in Business Administration, and has chaired or served as trustee for several educational partnerships, including the City of York Independent State School Partnership, the School Partnerships Alliance and The Shewsy. He is also a member of HMC and the G30 group of Schools.

Leo is married to Jules, a palliative care doctor, and they have three children who are current or former Salopians. The family, along with their cats, dog and assorted smaller creatures, enjoy exploring the Shropshire countryside together. Leo is a lover of sport, cricket and watercolour painting and supports both Arsenal and Shrewsbury Town FC.