Virginia Chadwyck-Healey on how to dress for work when you're over 50

Harriet Hathaway in a blue top
Harriet Hathaway Credit: Andrew Crowley at The Swan, Streatley 

Not many headmistresses would accept my plea to have them model for this column. But then Harriet Hathaway, of Harriet House school, has always stood out from the crowd. I am biased of course, but from personal experience, anyone who finds time for a mother on the brink of tears at drop-off (and incidentally on the brink of then discovering she has postnatal depression) stands out as being a good egg, a golden egg no less. (No I'm not trying to secure my youngest as Mary in the Nativity!).

Hattie is the eldest daughter of one of the 'Dawson Twins' who ran leading prep school Sunningdale from 1967 to 2005. Some of you will know exactly who I am talking about as many of you might be married to, parents of, or grandparents of a 'Sunningdalian'. Being passionate about education is what this family does best, but today Hattie is not only a headmistress, she is my style challenge as far as bust sizes go. This is one fashion conundrum I really want to address given the emails I have received on the subject.

Harriet wears leather loafers, £45, M&S; Satin Bib Longline Shirt, £35, M&S; Wide Leg Ankle Grazer Trousers, £25, M&S; Gold shell detail necklace, £245, Tohum at Net-a-Porter Credit: Andrew Crowley at The Swan, Streatley 

'You will have your work cut out!' said Hattie. Over hair and make-up for this shoot she continued, 'if I had 5 minutes with the creative people at the helm of some of the UK's leading high street brands, I would say 'don’t forget the 50 year olds and over.  We still have a lot of life left in us!'. As a headmistress, the need for 'day to night' dressing is key. The role requires well turned-out, approachable personalities and the same goes for their clothes. Their day consists of welcoming parents and children each morning to hosting parents, or prospective parents, for supper. Hattie specifically said she wanted to feel dressed for any occasion - so off I went. 

I have to be honest, the search for items that would work was indeed a challenge. I fully sympathised with her lack of enthusiasm for shopping because my research quickly felt more of a battle than a bounty of beautiful options. This is a woman who wants to wear colour and who doesn't want to just stick to 'slimming' black. After all, she finds her spirit in teaching 2 - 5yr olds. Black is no way to inspire them day in, day out. And yet not only was the list of colours available limited, so was the list of brands I could realistically pull ideas from. Many brands stopped at size 16. The conscious consumer in me also felt the need to work with brands that had good credentials and ethics (as far as I know) even if that drastically reduced the list of potential candidates.

Harriet wears Aria (green) blouse, £85, Boden; Wool blend coat, £225, Hope; Trousers, necklace and shoes same as before Credit: Andrew Crowley at The Swan, Streatley 

These two looks both focus on one gem-like colour pop that does the talking. On a slightly larger frame you don't want all the clothes to be too loud though. Instead, allow jewellery (leading the eye upwards to the face), shoes, appropriate make-up, and of course the actual person to do the talking. V necks, overt cleavage, buttons that strain...these can distract far too much.  Instead you want positive attributes to be talking points.  Ensure you choose a shirt/ trouser or jacket size that glides and moves with fluidity.  

The clothing I chose came from Boden, Marks & Spencer and Hope Fashion. Hope was the brand on everyone's lips at the photoshoot, and one I am sure will continue to gain traction amongst women of all sizes because it still feels like a 'secret find'.  They range from 'Super Slim to Super Curvy' and it won't surprise you to hear that founder Nayna McIntosh is ex M&S or that one of the backers is former M&S CEO and Chairman, Stuart Rose. 

Hattie said her team of staff were cooing over her hair and make-up when she returned to the school day. I hope today they are bowled over by their boss's no-fuss-but-vibrant look. And to any parents reading this, wondering what to give the school teachers this year? Make a mental note that a Trish McEvoy under eye concealer, a Benefit bronzer, or Charlotte Tilbury's 'Wonderglow' are much more original than any scented candle, hand cream or box of liqueur chocolates.  I guarantee you will be top of the class if you heed said advice.

Ginnie's staples this weekend...

Cell Repair Night Oil, £62, Aurelia at Victoria Health; Large Bolga Basket One-Of-A-Kind No.23, £55, Wovenology; Pureology strength cure shampoo 250ml, £13.95, Pureology at Feel Unique; Buti blue wash bag, £12, Molly Mahon

Virginia Chadwyck-Healey's column appears each Sunday in The Sunday Telegraph and is published online every Sunday at 8am on Telegraph Fashion.

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