Hat Trick: Top Hat-Wearing Tips

For a wedding, a big occasion or just because, what does a hat say? Advice from experts including the Queen’s milliner.
The right hat can be a real feather in your cap… but you definitely don’t want to look like a mad hatter. We ask three experts to give their advice on choosing the right hat for a wedding, one of the Season’s big events or just for everyday fun.
Celebrity personal stylist Isobel Kershaw, founder of The Stylist London, is one of the trainers on The British School of Etiquette’s lady etiquette course; Philip Sykes, the school’s principal and renowned etiquette expert, is also one of the course’s trainers.
Rachel Trevor-Morgan has a Royal Warrant of Appointment to the Queen, who has been wearing her hats for more than a decade, starting with her 80th birthday service at St Paul’s Cathedral. More recently Catherine, Duchess of Cambridge, has worn Trevor-Morgan hats and she works with designers from Bruce Oldfield to Caroline Charles.

1. When should you wear a hat?

Isobel Kershaw: Women can wear a hat anywhere – both indoors or outside, (with some restrictions). Men must remove their hat in certain company, to show respect – and at all times indoors.
Rachel Trevor-Morgan: All hat-wearing should be encouraged! At some weddings they will actively ask you to wear a hat – that’s an excuse to push the boat out. If you don’t know the organisers’ thoughts on hats, err on the side of classic and slightly down-played; you don’t want to upstage the wedding party.
Philip Sykes: A woman would remove a large-brimmed hat in church (so as not to block someone else’s view of the bride and groom) and at a wedding sit-down dinner. My grandfather (who would be 110 if he were still alive) always used to say never trust a man who drives with their hat on. I’m not sure why, though!

2. How do you choose the right hat?

Isobel Kershaw: Ensure the brim is no bigger than your shoulders and that it turns up at the front so your face can be seen and will not be shadowed in photos. Don’t let the hat be the statement of the outfit, or let it wear you; it needs to be the frame, to compliment the look and bring it all together.
Rachel Trevor-Morgan: You should keep things in proportion: if you are wearing a great big saucer with lots of feathers and flowers, it might be over the top. But the rules are quite difficult to put into words: you could have a big-brimmed hat which is quite simple and a dramatic silhouette. It’s great if you can have a hat made and get advice from a milliner but, if you’re going down the high street, take a friend, try on lots of styles and look at yourself in a full-length mirror.

3. What about choosing your hat colour vs your outfit?

Rachel Trevor-Morgan: There are no rules on colour. I like a co-ordinated look: if you have a very busy, patterned outfit, you don’t want a very busy, patterned hat. With a strong pink dress and coat, say, you might want a neutral colour for a hat, picking up a highlight of colour. Find the style first then think about colour.

4. What kind of hat should the mother of the bride wear?

Rachel Trevor-Morgan: There are no rules! You have an important role to play on the day; everybody wants to see you and it’s your moment, so go for it and lead the way in the style of the day.
Isobel Kershaw: The hat worn by Meghan Markle’s mother [American yoga teacher Doria Ragland] was rather understated and, as the mother of the bride, I felt she should have been helped in ensuring that her outfit [a mint dress and coat by Oscar de la Renta with a beret-style mint hat by Stephen Jones] was more of a statement for such an occasion and position.

5. Are the rules different for hats at a Royal Wedding?

Rachel Trevor-Morgan: The same rules apply as to any wedding, although the eyes of the press are on you. You have to make an effort and look your best, but you don’t want to draw attention to yourself too much.

6. Is a fascinator suitable headwear?

Isobel Kershaw: I have never liked fascinators; they do not reflect a refined style or give a ladylike finish to an outfit. I am relieved that they have been banned from Ascot. Having said that, the “modern take” – as worn by Lady Kitty Spencer (a green pelmet with angular spiky ‘feathers’ and a net) at her cousin Prince Harry’s wedding – can look stylish and elegant.
Rachel Trevor-Morgan: I think we’re over them a little bit. They’re great if you’re going to an evening event but, if you’re going to a wedding, it is much better to do more of a hat – even if it’s a pillbox or beret/ button shape. A few feathers and a comb will enhance your hairstyle, but doesn’t do the same as a hat.

7. What’s the right hat for a man to wear?

Isobel Kershaw: For summer, a stylish and flattering trilby is a great option for events such as Ascot, Henley and Wimbledon. Be aware that they should be removed if blocking someone’s view when seated. Baseball hats are very casual but have their place; beanies are also casual and not flattering on an older man.
Rachel Trevor-Morgan: It’s not so much my area but I work at the back of the gentlemen hatters Lock & Co and I think men in hats look great. I like to keep men’s hats traditional and I love that formality; I’m not a fan of a quirky hat – a coloured top hat or the like.
Philip Sykes: Men can wear a top hat with a morning suit; it should be worn on the front of the head and removed and carried under the arm once indoors. The wearer should know how to ‘doff’ their hat i.e. how to raise it above the head to greet guests.

8. Who wears a hat well?

Isobel Kershaw: The ladies of the Royal Family all wear hats the way they should be worn, with elegance and decorum. I always seem to admire outfits worn by Camilla, Duchess of Cornwall – she looks very regal. I felt that Victoria Beckham’s hat for Prince Harry and Meghan Markle’s wedding was a little ‘funeral’.
Rachel Trevor-Morgan: I like to see women wearing hats that are beautifully co-ordinated, rather than ridiculous things. With the hats I make, I am trying to make women look beautiful and elegant. That isn’t to say you can’t have fun with it. The Queen is very at ease in hats and wears them all the time.

9. What does a hat say about you?

Isobel Kershaw: Wearing a hat today is not as important as it used to be. Men and women always had a hat when they left the house, whatever the occasion – but today a hat is worn in a different way. The styles can be more casual – most popularly to keep out the sun or cold. A hat can also be a status symbol or project one’s personality.
Rachel Trevor-Morgan: These days we are not so used to wearing hats, so it is actually a much bolder step than it used to be, when everyone wore them all the time. Hats can require a little bit of extra confidence, but they should also give you confidence.

10. How do you store, clean and look after your hats?

Isobel Kershaw: Hats are difficult to clean and should be packed inside the crown with tissue paper and covered with tissue, in a box. Keep it in the shade, as the sun can bleach fabrics such as straw.
Rachel Trevor-Morgan: Make sure the hat doesn’t sit on its brim and sink down. Common sense says you should protect feathers and bows and not squash any trimmings. Cleaning can be a little tricky – you can sometimes use baby wipes or cleaning fluid but, if in doubt, take it to a professional