'The watch is Head Boy of men’s accessorising': Ginnie Chadwyck-Healey and Tom Chamberlin's Summer Season style secrets

For the ladies by Ginnie Chadwyck-Healey

It was Cheltenham Gold Cup day 2025 that proved we are heading in the right direction. As much as we saw many racegoers sporting the classic head-to-toe tweed, top-handle bag, suede boots and trilby hat, one lady — interviewed on television — stood out for me. Her entire outfit had been upcycled, reworked and re-accessorised, all from her own wardrobe. On a day of fast racing, slow fashion was the winner. She was colourful, confident and quite different — her style entirely her own.

It’s possible some of you have a drawer brimming with heirlooms, Granny’s brooches, silk scarves, evening gloves, pocket watches — an odd assortment of things we aren’t quite sure how to bring back to life in 2025. Times move on, but fashion is forever cyclical (I must have written that thousands of times over the years) and, as we approach the Season, with all its whimsical touches, dress codes and formalities, it’s the accessories to which we need to pay close attention.

Comfort is queen

I maintain that the art of accessorising — indeed, the art of style — has a lot to do with comfort. You can wear the greatest dress, slip on the prettiest heels and don an eye-catching hat, but if any part of that outfit is remotely uncomfortable, you’re in for a long day of pain. Too cold in a long, wafty dress at Henley? Even if you can borrow a Leander blazer from a friend, that’s an entire day’s outfit lost to poor planning. Shoes pinching as you enter the Royal Enclosure at 10am… by 10.28am, you’re on the hunt for a Compeed plaster. Rain stops play at Lord’s (it’s England, after all) and you’ve only got that free (unsightly) umbrella emblazoned with some big corporation’s name? Not the done thing. Half-time divot-stomping at the polo, yet you’re in stilettos and sinking into the lawn? Rookie error.

Simply the best

The etiquette of accessories is easy; keep it simple. Don’t carry an umbrella or bag that’s too large or impractical. If you use a fan to cool you down (elegant and demure if it’s a traditional hand-held one, a whirring, battery-powered example is far too ‘Christmas cracker’), avoid overusing it to the point where you’re swatting away your own elegance. For seeking shade from the sun, a baseball cap is definitely too casual and a wide-brim sunhat is fairly likely to annoy your neighbour. Instead, try a chic rattan visor for the ladies and a Panama for the gents (unless it’s Royal Ascot, but you know this).

For keeping warm, always have a layer that isn’t obviously an afterthought, should you get too cold. A big dollop of a navy blazer will ruin the delicacy of a pretty dress. Try a shawl (Hera Cashmere is a lovely option) if you can’t find the right formal jacket. Always road test whether the layer fits, rolled up, in your bag.

Match made in heaven

You might choose to invest in a new bag from names such as Strathberry, Mashu, DeMellier or Aspinal of London, but don’t attempt to match it to the colour of an outfit. You’ll never use it again if you do, I assure you. Instead, consider metallics (avoid glitter; too ‘party’) as a neutral, because such bags are smart and easy to find when you don’t always want to have cream, nude or peachy accessories. Metallics will have staying power in your wardrobe long after the summer.

As for ‘matchy matchy’, it doesn’t have to be a precise match between the colour of your outfit and accessories. Case in point: The Princess of Wales at the Commonwealth Day Service last month. Her outfit had two different reds at play (tomato and crimson), but she married them into a neat synergy by ensuring that her hat exactly matched her shoes (and, indeed, the red chairs of Westminster Abbey). She didn’t do matching coat, bag, hat, shoes as she might have done in the past, displaying the confidence of matching just enough, but not every single aspect.

What, this old thing?

Sometimes, it’s simply not feasible to splurge on an expensive accessory you might wear only once. The good news is that hiring or renting accessories (or even the whole outfit) is the norm in 2025. (A study by Westfield shopping centre found the UK clothing rental market has a potential value of £923 million).

One of my favourite British milliners is Camilla Rose, who reports about 60% of her business is now rental. ‘It gives people flexibility to explore more hats without the commitment. Those who do purchase often have more than one outfit in mind and we are happy to tweak previously purchased hats.’ Generally, with the focus on circularity in fashion (reuse, rewear, recycle), ever more brands are happy to offer tweakments to designs and that’s where you, the customer, can engage your own ideas. Haberdashery heaven V V Rouleaux has a treasure trove of trimmings to revive previously worn accessories. Ribbons, buttons, butterflies, feathers, flowers on wires — for the experimentalists among us, these are often the most attractive part of the Season.

It’s all about balance — find the sweet spot between functionality and style and, remember, accessories should enhance, not overwhelm, your outfit. Follow the etiquette, embrace the formalities (know the terrain!), but, importantly, have fun with it. Accessories are your chance to add personality and a touch of flair; for men, tie pins, neckerchiefs and pocket watches are up there. Hats are my favourite and I still have a James Smith & Sons ladies umbrella on my wishlist. Then there’s the velvet opera coat longing to go out, currently destined for my children’s dressing-up box…

My final and most practical tip?

Take a handbag with handles long enough to hang from a wrist or shoulder so you can go hands free. How many times have you wanted to hold a glass of fizz in one hand when studying a race card, but had awkwardly to clutch a bag? How many times have you not had hands free to clap the speeches at a wedding? How many times have you wanted to shake hands only to realise you’re proffering… an elbow. No more! Is that me trying to help you justify a new handbag from Mashu? Perhaps…

For the gentlemen by Tom Chamberlin

For years now, a rather dashing German gentleman has trotted into the Royal Enclosure at Ascot in immaculate morning dress, complete with a stiff collar, cane and spats. He looks very fine and is a grand reminder of the Edwardian era, when everyone dressed like that. Standards of dress have certainly slipped since then and his valiant resistance is to be commended, but when it comes to accessorising, he does need an update.

Accessorising offers the true wheat-chaff-sorting exercise, sartorially speaking. A bespoke suit is a wonderful thing, but there are great ready-to-wear options that will send you out into the world a new man. What distinguishes the best dressed is how they accentuate a dress code with flourishes that set them apart.

On your own head be it

There was a time when hats were ubiquitous for men. The sad decline is an impediment to any truly stylish society, but the summer will still probably require any of three hats — the top hat, the bowler hat and the Panama hat. A top hat is the most formal option and should only be worn with morning dress or white tie. Although it is de rigueur in the Royal Enclosure at Ascot and at Buckingham Palace garden parties, it is not something I would recommend for a wedding. You will regret carrying it around all day between the service and reception and trip home. Renting a top hat is, to some extent, fine, but if you are regularly going to events in the summer, it will become a false economy when you could buy one that will last you the rest of your life.

If you want to be really smart, try to find one made in vintage silk. The silk plush you see on these hats cannot be made any more after a brotherly brouhaha that resulted in the factory burning down and the last of the machines that made this fabric being lost.

The bowler hat is largely for cavalry and guards officers, who have various marches in May. Owing to royal attendance and vast numbers of dashing officers keen on a convivial luncheon, these tend to become something of an occasion.

The Panama hat is for any occasion that requires some level of dressing up and being outdoors. From Wimbledon to Glorious Goodwood, Henley to the RHS Chelsea Flower Show, you should have something that shields you from the elements and a hat appropriate for a jacket and tie. Fedoras are fine, but the beaver felt you’d most commonly find with it can make things quite warm, so the breathability of the Panama, not to mention the smart ribbon that can correspond with your old regiment or club, is much more fun.

Come rain or shine

From a historical point of view, some say, the umbrella offers a great distinction between us and the French. Our friends across the Channel eschewed the umbrella years ago because, according to a French 18th-century magazine, to have one meant you could not afford a carriage. In Britain, since the days of Sir Walter Raleigh, we have taken sodden clothing with great cultural pride, so being out in the elements when it rains is par for the course and an umbrella is not even meant to be used if the rain comes. Have a look at old images of people such as Anthony Eden and the tightly furled umbrellas they carry with them. A guards brigadier once told me that, to get the umbrella looking like a scabbard, they would remove the metalwork inside, rendering the umbrella useless as a means of shelter.

My recommendation is to have an umbrella on your person at all times. It helps with posture and is a great opportunity for chivalry, as long as it works.

Jacket ephemera

The jacket is where most good accessorising can take place. There are some rules to adhere to, but these aren’t defined by a dress code, so you can use artistic licence. A pocket square and tie should be bedfellows, but never match — this is naff (and a bit Pete Hegseth). Instead, they should have some colour co-ordination and support the jacket, rather than stand out from it. Lapel pins, chains and boutonnières are smart, but, again, wear in a cautionary manner. They should be relevant to you, as people will ask about them. I sport a 1950s Dunhill lighter as a lapel chain: it was my grandfather’s and people derive great joy from seeing it work.

Follow, for example, the sturdiest of the Royal Family, Mike Tindall. Although his physique creates a bit of heavy lifting for clothing to flatter and cope with the scale, he emerges with a lot of plus marks through his accessorising. His tie often matches the outfit of his wife, Zara, a sweet detail, and he turns to tie bars and lapel pins to fill the vast expanse of his chest and shoulders. Indeed, at Ascot, he is often the very best dressed.

Wristy business

The watch is Head Boy of men’s accessorising. It is a complicated topic and there is no way of simplifying it without upsetting an industry that has poured billions of Swiss francs into development, engineers and tiny components all designed to track the passing of time accurately.

However, I think there are two types of watch you can consider for any social occasion: the sports watch and the dress watch. The former should be worn with anything that is lounge suit or less formal and the dress watch is for a lounge suit and more formal. The distinction is the dimensions and strap. A dress watch usually comes with a leather strap and slimmer watch (although this is not always the case, metal straps for formal occasions can be very smart indeed). There are those who say you shouldn’t wear a watch with black tie as you should be enjoying yourself without any need to know the time. This is rubbish, as dress watches for eveningwear have been made as long as there have been wrist watches.

Sports watches usually come with a linked metal strap, often steel, but, if you have gold, then good for you. Some sports watches are inherently very smart. Mark Birley wore an Audemars Piguet Royal Oak with his formal attire and, if a sports watch was good enough for him, then it is good enough for you.

Well trodden

Socks are simple. They should be navy blue, which works for everything except black tie, when black should be worn. Alternatively, they can coordinate with another part of your outfit. I like to wear sky-blue socks to match my morning-dress waistcoat. Patterns are a no no and try to get knee-high socks, as you should never show hairy skin when you cross your legs.

Shoes are the most important element of a look. They should be black for formal attire, such as morning dress or black tie. With a suit, black is appropriate for a navy one, but not much else. When wearing grey, you should go brown (not tan, ever) or burgundy. These two colours of shoe work for anything lighter than navy, so make sure they are in your roster and, of course, they should all be well polished, too.

As for spats, the Buckingham Palace garden party apparently witnessed their demise when George V once emerged not wearing them; guests quickly removed theirs and disposed of them in the bushes.