'One of the greats of his generation' - Shrewsbury headmaster named 'Best Head of a Public School' at national awards
The headmaster of a Shropshire school has been named the 'Best Head of a Public School' in a prestigious national education awards scheme.
Leo Winkley, headmaster of Shrewsbury School, received the honour in the Tatler Schools Awards 2026.
The award, which is voted for by parents and the wider school community, is in recognition of his impact and leadership since his appointment in 2018.
Under his stewardship, Shrewsbury School has worked to preserve its 473-year heritage while embracing innovation and a "whole-person" approach to education. The school was named the 'Independent School of the Year' in 2020.
Mr Winkley has also overseen the expansion of the 'Shrewsbury family of schools', which now includes eight schools around the world - from Hong Kong to Cambodia, and more recently, the addition of Terra Nova in Cheshire.
Inspired by old Salopian Charles Darwin, the headmaster frequently references "survival of the kindest" in his vision for education.
"Receiving the Tatler Schools Guide 'Best Head of a Public School 2026 Award' is deeply humbling," said Mr Winkley. "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!"
Since 2020, Shrewsbury School has received a number of awards and accolades, including being named as a 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; and awarded the Oppidan Gold Mentoring Award.
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."
Dr Joe Spence, chief executive officer of the School Partnerships Alliance, added: "Congratulations on the award. 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."
