School leaders spend so much time thinking about curriculum, safeguarding, and staffing that sometimes the basics—like what to wear to work—get overlooked. Yet, as many headteachers know, your wardrobe can affect how comfortable, confident, and approachable you feel each day.
Recently, in the HeadteacherChat Facebook group, one member asked:
“Where do middle-aged female headteachers buy clothes for school? And what do you wear on your feet? I feel I need to update my wardrobe!”
The post sparked a lively discussion with over 90 comments, ranging from high-street staples to second-hand bargains, as well as some passionate words about being yourself.
Popular Clothing Choices
Many headteachers agreed that comfort, practicality, and affordability are the top priorities. Here are some of the most recommended brands and approaches:
- High Street & Supermarkets: Next, M&S, Sainsbury’s, Tesco, New Look.
- Mid-Range & Stylish: Boden, Hobbs, Whistles, Joules, White Stuff.
- Sustainable Options: Vinted was mentioned repeatedly as a go-to for bargains and sustainable fashion. Charity shops were also highlighted as a great way to find Hobbs, Jigsaw, and Phase Eight dresses.
- Statement Brands: Popsy Clothing, The Fold, Oliver Bonas—especially for those wanting to bring colour and personality into the role.
Footwear: Comfort Over Heels
If there was one clear theme in the discussion, it was this: heels are out, comfort is in.
- Everyday shoes: trainers (often black leather), Clarks, Reiker, Fly London wedges, and Doc Martens were all popular choices.
- For special occasions: heels still make an appearance, but only when required for formal events or key meetings.
As one headteacher put it:
“I dress like I mean business – and I always wear heels!”
But many others admitted that their heels now stay mostly in the cupboard.
Authenticity Matters Most
While the practical tips were useful, the most powerful theme was authenticity.
One member wrote:
“Be you! I used to feel I had to dress a certain way to feel like a Head – now I know how silly that was.”
Another added:
“There is no Headship uniform – and if there is, I’m so not here for it!”
From bold tattoos and bright hair to quirky prints loved by children, many headteachers shared that their personal style has helped them connect more deeply with staff, pupils, and parents.
Takeaway for School Leaders
Choosing work clothes as a headteacher isn’t about following a strict dress code. Instead, it’s about balancing:
- Professionalism – looking put together for parents and governors.
- Practicality – being able to crouch down with children or dash across the playground.
- Personality – showing authenticity through your style.
Whether you’re browsing Boden sales, finding treasures on Vinted, or rocking Doc Martens with a dress, the key is this: wear what makes you feel confident, comfortable, and unapologetically you.
What’s your go-to outfit for a busy day in school?
