So which era had the most flattering look for men? 

On the whole, men tend to assume that trends in fashion and grooming are women’s business. Liquid lipsticks and ‘contouring’ largely pass us by. 

But when I read a recent Femail piece that looked at more than 100 years of women’s fashions, I was intrigued — and decided to open up the Deedes family album to see how things have changed for men. My mother was delighted to help, sending me a deluge of photos and quirky stories.

But could I pull off any of the top men’s styles of the past 100 years today? With clothes advice from Russell Howarth, head cutter at City tailors Graham Browne, and hair and make-up from wig expert Amanda Clarke, I found out which trends have stood the test of time . . .

Henry Deedes (pictured today) recreated the iconic styles of each decade with the help of images from his family album to discover which trends have stood the test of time


I must say, I’m a fan of this 19th-century look. I’m no hipster, and normally hate wispy beards — but, styled with a gentleman’s morning suit, these whiskers add gravitas.

I wear something similar to this outfit to Ascot each year anyway, so it is a look that has lasted. My friends do say I dress like someone from a past century — perhaps it’s no surprise I’m a fan!

My mother was gleeful when she dug out this be-whiskered picture (inset) of her great-great-grandfather, Major Herbert Mackworth Clogstoun — she insists we look alike. He received the Victoria Cross, Britain’s top award for gallantry, in the Indian Mutiny in the 1860s, before being killed in action.

Pictured, Henry's mother's great-great-grandfather,  Major Herbert Mackworth Clogs­toun

Henry (pictured) says he wears a similar suit to the style of the 19th century to Ascot each year however today's material is lighter

Henry (pictured right) says he wears a similar suit to the ones worn in the 19th century to Ascot each year, however today’s material is lighter according to tailor Russell Howarth

He had great facial hair. Beards were big back then, a trend that started in the Army during wars in India — a bushy beard was a sign of authority. To get the look, wig expert Amanda Clarke plastered on custom-made whiskers, with my hair parted just off centre.

Tailor Russell Howarth says: ‘Light merino wool didn’t come in until the Fifties, so a typical suit [of this time] might weigh 19oz compared with 10oz today and have the texture of sandpaper.’ Ouch!


With my hair slicked back, I could be in a P. G. Wodehouse novel. It’s easily my favourite look: masculine, smart, but not stuffy. I’d happily dress like this now, and I think it’s appealing to women, too.

My great-great-uncle Wyndham Deedes, Colonial Secretary in Palestine in the 1920s, certainly adopted the hairstyle — although worn with sober, formal clothing for official duties.

Pictured, Henry's great-great-uncle Wyndham Deedes, Colonial Secretary in Palestine in the 1920s

Henry (pictured) believes the slick-back hair of the 1920s can still be worn today

Henry (pictured right) believes the slick-back hair of the 1920s can still be worn today 

Prince Edward (later Edward VIII) inspired a generation of dandies in the Twenties, says Russell Howarth. ‘A dapper chap, he developed a taste for sharper tailoring and pleated trousers — a new invention considered daring.’

Being clean-shaven was the norm: the disposable razor, patented in 1904, meant beards came to be seen as unhygienic. Brilliantine oil made men’s locks glossy — wives knitted doilies to cover the backs of chairs and protect against greasy heads.

Although he wasn’t born until decades later, I think I look a bit like my dad here. He’s been gelling his hair like this for years.


There’s a definite resemblance here to my mother’s father, Major Elwin Gray, pictured in his Army uniform in the Thirties with a manicured moustache and glossy hair. He looks very dashing. But can I really get away with this ’tache?

It was certainly the look of the decade. The Hollywood studio system was churning out such immaculately dressed icons as Cary Grant and Gary Cooper. 

Pictured Henry's mother’s father, Major Elwin Gray

Henry (pictured) questions if the thin moustache trend seems out of place in today's style

Henry (pictured right) questions if the thin moustache trend would be seen as out of place in today’s style

Men followed suit with gelled hair, side partings and thin moustaches that made a film-star scowl all the more dramatic. ‘It was a groomed look,’ says Amanda. ‘Facial hair was limited to a pencil moustache.’

But the ensemble makes my mother giggle — and I think I’d get teased even more for being old-fashioned if I tried to grow a moustache.

I don’t think I can carry off a military uniform. But the shirt and braces I’m wearing instead aren’t that far from my usual office attire. ‘This was the start of a golden age for tailoring,’ says Russell. ‘Yarns were finer, creating beautiful suits with flowing shapes.’


The Forties were the decade fashion forgot, thanks to clothes rationing.

This Fair Isle jersey looks like the stuff of style nightmares — though I notice they’re all the rage in shops at the moment. Somewhat disconcertingly, a female friend says: ‘You do actually look quite dapper.’

Meanwhile, without pomade, my hair has resumed its natural springiness and my clean-shaven face suddenly looks about five years younger.

My paternal grandfather, Bill Deedes, served in the King’s Royal Rifle Corps throughout World War II and was awarded the Military Cross in 1945 after an enemy attack in the Netherlands.

Pictured, Henry's paternal grandfather, Bill Deedes

Henry (pictured) believes popular clothes from the forties are all the rage at the moment

Henry (pictured right) believes popular clothes from the forties are all the rage at the moment

He’s wearing a Lieutenant’s uniform in this picture, although he later made it to the rank of Major.

I can’t imagine him in a jumper like this — he was a formal dresser all his life — but my grandmother kept sheep and was an avid knitter, so it’s safe to assume he wore a few in his time.

Women on the Home Front were encouraged to knit for the troops, which, says Russell, was the start of Britain’s obsession with the chunky sweater.

‘Up until this point, gentlemen wore waistcoats, but knitwear became more prevalent and you started to see woollen tank tops.’

The Army required soldiers to be clean-shaven, but many were growing their hair longer and wearing it without pomade. Rationing meant most men clung onto suits from the previous decade.


This quiff is magnificent — but, at 39, I think I’m a little old to be dressing up as Elvis!

Still, in the Fifties, this look was de rigueur as the post-war baby boom led to the birth of teenage culture in Britain.

The clothes, on the other hand, could be from a modern-day shop. Young people began embracing U.S. trends such as denim jeans — originally designed for American cowboys and miners — and leather jackets, as well as the cotton T-shirt, inspired by James Dean and Marlon Brando in films such as Rebel Without A Cause and The Wild One.

Pictured, Henry's grandfather Bill

Henry (pictured) says the clothes of the fifties could be still worn today however the hairstyle is questionable

Henry (pictured right) says the clothes of the fifties could be still worn today however the hairstyle is questionable

Even respectable junior ministers — my grandfather Bill had, by now, given up his officer’s togs for a role in Government — experimented with new looks such as this rather fabulous shawl-collar sheepskin coat.

But, thankfully, he stuck to a less fussy hairstyle.

Elvis’s personal stylist Larry Geller has revealed he used to shampoo and massage his scalp every day, before brushing his hair 50-60 times. ‘To have that rockabilly look, hair needs plenty of body, so men would have it blow-dried before combing it back,’ explains Amanda. ‘Brylcreem became more mainstream around now, so it was possible to style hair, but leave it feeling soft.’


When I left Eton in 1996, the country was gripped by Britpop fever, with bands such as Oasis sporting the shaggy haircuts of the Sixties. I let my hair grow out for a few years, and the result was not too different to this.

Of course, the first time around, the Sixties mop top was inspired by the Beatles, with every teen boy in Britain following suit. Except, that is, my father Jeremy.

Pictured, Henry's dad

Henry (pictured) says he previously grew his hair similar to this sixties style in the 90s

Henry (pictured right) says he previously grew his hair similar to this sixties style in the 90s

In this photo, my dad wears a buttoned-up shirt, V-neck jumper and skinny tie — clearly still channelling the clean-cut look of the previous decade. The Deedes clan has never been big on teenage angst.

In terms of fashion, ‘people started going for the mod look’, says Russell. ‘Zips were popular and merino wool was readily available, so suits were comfier.’ Sadly, this polo neck is doing nothing for my jawline.


Amanda has done a wonderful job recreating a typical disco-inspired hairstyle but, dear God, I am dying with embarrassment at the result! One look at this cringe-inducing picture and I think we can all agree it’s a look to consign to history.

While long hair on men had previously been considered a sign of decadence, in the Seventies it became as common on middle-class men as on hippies. Even senior politicians began sprouting bushy sideburns.

Pictured, Henry's father with longer hair than usual

Henry (pictured right) believes the styles of the seventies should be left in history

Henry (pictured right) believes the styles of the seventies should be left in history 

My family approached this madness with caution. This photo of my father shows him with undeniably longer hair than usual (it’s even hanging over his collar), but nothing like the extravagant bouffant I’m modelling.

His stripey shirt, however, is pure Seventies and matches the shiny one I’ve got on remarkably well. He looks masculine, though, whereas I think mine could have come from the ladies’ section of a bargain basement.

Russell says this was a tough time for tailors. ‘Before, most men would have a couple of suits made a year — at Easter and Christmas. But Seventies’ lads just wanted to go down the Kings Road and buy jeans and a few colourful tops.’


I think I resemble Duran Duran’s Simon Le Bon with this hair. His image adorned every teenage girl’s wall — even Princess Diana was a fan. But, let’s face it, the style has dated badly.

The T-shirt under a blazer look, however, is here to stay — it’s not to my personal taste, but you can find the style wandering down any British High Street on a Saturday night.

Growing up in the Eighties, I recall my father smartening himself up in the mirror each morning before leaving for work in Fleet Street.

Pictured, Henry's dad

Henry (pictured) says although the t-shirt under a blazer fashion style is still popular, the hairstyles of the eighties now appear dated

Henry (pictured right) says although the t-shirt under a blazer fashion style is still popular, the hairstyles of the eighties now appear dated

With his hair slicked back with Royal Yacht lotion, business suits and sometimes two-tone shirts, he was more Michael Douglas in the 1987 film Wall Street than George Michael.

The thought of Dad boarding the 7am train to Paddington in the Eighties with a mullet like this makes me chuckle. ‘It’s almost two haircuts in one,’ says Amanda. ‘You have all these layers on top, but also the mullet at the back.’

To tame those layers, mousse and gel were popular and, for the first time, men were openly getting highlights and dyeing their hair. This was also the start of designer stubble — the Eighties have a lot to answer for.

As for suits, it was all about shoulders, says Russell. ‘I remember cutting jackets with a 42 in chest and nearly a 7 in shoulder. Everyone wanted to look like Don Johnson in Miami Vice.’