'The problem with men today," begins Philippos the barber, as he holds an open razor to my throat in Trumper's salon in London's St James's. Oh dear, I think, as our eyes meet in the mirror, there is no way this sentence can end well.

I'm reclining in a barber's chair, my face is tingling. This is because it is bathed in rose-scented, glycerine-rich coral skin food. Of course it is. My stubble is softening thanks to hot towels and the violet-scented shaving cream that has just been applied with a badger-hair brush. Philippos argues that badger hair is essential to soften stubble effectively; badgers, you I suspect, would disagree.

I am eager to know how Philippos's sentence will end because I am at the start of a journey of male self-improvement. At the age of 48, balding, stooping, disappointingly paunchy, with no dress sense, with one suit that I last wore five years ago to my dad's funeral, with minimal grasp of – as the French would put it – savoir vivre, I have decided it is time to up my game as a man.

Perhaps this is a mid-life crisis. Or, at least, one of the many that litter one's declining years. As a man, I have always felt like an amateur, a boy rather than the finished article. There is a scene that captures this in Seinfeld. Jerry and George are kvetching in a coffee shop. Jerry: "What are we doing? What in God's name are we doing?" George: "What?" Jerry: "Our lives! What kind of lives are these? We're like children. We're not men." George: "No, we're not. We're not men."

Sooo not men. It would be easy to surrender to the prevailing zeitgeist – to just buy a fleece and some slippers, take an interest in Strictly Come Dancing or Doctor Who memorabilia and cover that bald dome in a hoodie and beanie combo. Instead, belatedly, and in a very new-leaf way, I choose otherwise: I will strive to get on first-name terms with my tailor and I will outgrow that ubiquitous slouching phenomenon, the male kidult.

Three things prompted this journey. One was watching Mad Men. Not so much season four, when Don turns into a secretary-seducing moral vacuum of a loser lush, but seasons one and two. What man – straight or gay – wouldn't want to look as good as Jon Hamm's Don Draper in that era before Betty (understandably) binned him? The sharp mohair suits; the pert tilt of the trilby; the aura of sexual confidence; the acquired ease of manner; the delightful, if career-ruining, possibility of being drunk off your ass at your workstation by 10.30am.

When did men stop dressing as well as Don Draper or Roger Stirling? And why? Why can't I breeze into a cocktail bar and nonchalantly order something that commands respect if not quite awe? When did it become OK for men to wear fleeces in winter, to sport singlets in public and sandals disclosing ugly toenails in summer. When did we let ourselves go so much as to permit beer guts to swell our fatuously logoed T-shirts all year round? Something has to change.

The second thing that set me on this journey was thinking about my paternal grandfather. Grandad Jeffries died before I was born, but is still spoken about in our family as quite the clothes horse. He was a working-class man among whose jobs was working as a stoker for the merchant navy. During the second world war he worked on convoy ships to Murmansk. I imagine him shovelling coal in the ship's bowels, while feet away the North Sea was all ice to his fire. He probably expected to be torpedoed any minute. And then I imagine him back in Wednesbury, spending his hard-earned on a sharp suit. Time was when working-class Englishmen looked sharp, money or no. My maternal granddad wore collar and tie to the beach. He unrolled and smoothed down his trouser legs after a Blackpool paddle. Out of deference to their memories, I want to shape up.

The third thing was digging out an old Pavement album and listening to a song called Embassy Row. "Where is the savoir, where is the savoir, where is the savoir faire? He's not here no more." That line captures how I feel. Where is my savoir faire? He left after I bought a £10 Primark corduroy jacket.

This makeover isn't, perhaps, the sort of thing I should undertake while Britain is being scythed by cuts. Surely I, like everybody else, should knuckle down. Surely I, rather than savour the good things in life, should be copying the colleague who photographs the back of his head with his cameraphone to check he has shaved his head evenly. But that way madness lies.

Back to the barber's. "The problem with men today is that they don't know how to look after themselves," Philippos says. These days at Trumper's, the men who get wet shaved are mostly redeeming gift vouchers presented by wives or daughters. "Women go to spas and have a great time," says Philippos. "But men today don't. They used to, in the 18th century or whenever. We need to get back to that tradition."

Men used to enjoy the sensual ritual of being wet shaved. And then, shorn and fragrant, they would visit their tailor. In my eyeline as I recline are illustrations of 18th-century sophisticates, men who knew how to take pleasure and who weren't alien to thinking. I'd rather be Goethe than Wayne Rooney, you feel me?

Philippos starts to shave me. I think terrifying thoughts: of Sweeney Todd and other bloody storylines that make lying back and feeling pampered unlikely. But it's not so much a question of trust that's at issue here; rather a fear of abandoning myself to a pleasure. Which, however you look at it, is pretty sick. Plus, the last time I was reclining in a chair at the mercy of someone wielding sharp tools was at the dental hygienist's. There is nothing that so completely destroys any flirtatious vibe as your hygienist removing tartar deposits.

Philippos asks me a question that turns out to have great significance: "Do you shave up or down?" he asks. Both, I say. Philippos is too polite to say: "Well, here's the news, chump. You've been doing that wrong for 20 years. And you call yourself a man?" But he does point out that to drag one's Gillette Mach 3 upwards through my neck stubble – as I have done for many years – has damaged my skin. "You should be able to get a very close shave by shaving with the grain so long as your blade is sharp enough."

This reminds me of a scene in Whit Stillman's film Barcelona, when one preppie American who has been agonising over the correct way to shave ("I think I may have been shaving wrong my whole life") finally finds another guy who can induct him into this great male mystery. "So, what is the right way to shave?" "First, you wash with hot water . . ." And then these two guys walk off camera and we, the audience, who would really like to know how, never learn. Stillman's gag in cutting the scene here, I think, relies on the poignant truth that masculinity is a mystery play performed by those few who have been admitted, while the rest of us schlubs wait in the wings, baffled and unworthy.

"Would you like some after-shave?" asks Philippos. Absolutely. "Which?" Surprise me. "This is Eucris. Ian Fleming got 007 to wear it in Casino Royale." He splashes some on my face and giggles: "Now you're James Bond." If only.

I walk through St James's, inhaling Eurcis's olfactory combo of currant notes and lemony coriander, thinking: perhaps it's not too late. True, to acquire the gym-buffed embonpoint Daniel Craig brought to his performance as Bond at this stage in my life might be a little beyond me, but I could be some kind of a man. Maybe. At least now I know how to shave. Thirty-five years too late, but still.

I am going to see a tailor. Charlie Allen has made suits for Fabio Capello and Prince. "Do you know how much a bride spends on a wedding dress on average?" asks Allen. Not a clue. "£2,500. And the groom? £250. You can't tell me that's right." I can't: it's a big ball of wrong. What happened? "Grunge. In the 60s there were mods in sharp mohair suits and then we lost it." But you never did? "Nah. My dad was a tailor. I used to go to primary school in mohair shorts, and for secondary school, my dad tailored me a waistcoat. I've got too much self-respect to dress in a slovenly way."

Allen is a third-generation tailor who has been suiting north London's dressiest men (including the Arsenal football team, but let's not hold that against him) for 25 years. "When my dad had his business on this street [Upper Street, Islington] there were eight or so tailors all making suits. Not just for rich men. Pretty much every man would have a tailored suit. In those days, suits were things you bequeathed to your son. So that's why the seams would be so deep and there would be so much cloth that you could get let out. It's exceptional for a son not to be bigger than his dad, so that's why suits were cut so generously."

But enough about olden days. Allen asks: "Why do you want a suit?" Good question. What I don't want it for is workplace uniform. I've been there and I didn't like it one bit. The suit became a dead item of clothing I was obliged to wear from Monday to Friday. It wasn't something I associated with elegance or pleasure. Now, though, I want to put on a suit to make myself feel stylish, as though I am looking after myself and as though I am worthy to be my partner's date. So I need a suit for special occasions and for those wet Wednesday afternoons when jeans don't do it, when I want to look the business just for the sake of looking the business, you know?

"I do indeed," says Allen. "Well then, seeing as you're interested in Mad Men, what about a mohair suit?" He shows me some fabric, a 90% mohair swatch with a black warp and two ends of blue in it. We stand by the window to savour its light effects for several happy minutes. "That's a famous 60s fabric. This stuff used to be £6 a metre now it's £150. In the olden days, heavier fabrics were common in English suits. Even in the 60s, those mods would have been wearing three-ply suits. Now, because of central heating and air conditioning, you can wear one-ply and still look as sharp. I'll make you look sharp, don't you worry."

Then Allen measures me up. I put on a jacket that is being prepared for the CEO of Arsenal FC. It fits me well. "One thing about suits," says the photographer, "is that you can't help but stand up in them properly. You look about three inches taller and your posture is much better." Involuntarily, I have thrown back my shoulders, as if to treat the suit with the respect it deserves. In this united fleecedom of today, the reverse is happening: we are slumping in harmony with our shapeless outer garments.

I had thought that the next stop on my makeover journey would be a deportment class to unravel that Monty Burns-style hump looming in my back, but maybe if I spent money on a proper hand-made suit I needn't bother with other postural remedies. The suit would do the work for me. Don't give me that sceptical look.

We cut to the chase. How much for a one-ply mohair suit, two pairs of trousers, in the classic cut beloved of Arsenal senior management that would make me look like a cross between Don Draper and a soigné mod of the old school? "£3,500 plus VAT," says Allen. "Much cheaper than Savile Row; 50% up front and 50% when you're happy."

Here comes that laugh I predicted. I could have a new bathroom fully tiled, with sumptuous flooring and a nice paint job for that. But that is how old Stuart would argue. Despite all these positive thoughts, I can't commit to an outlay that will earn me a WTF call from my bank. "Don't be a stranger," says Allen as he shows me to the door. After all, how would my partner feel if I spent that much? "Angry," she says. Later she sends me an email (she must be angry): "If you're going to spend money on clothes, you should buy one very good-quality thing rather than filling your trolley to the gag reflex point in Primark." Am I the only one sensing hostility here? "Women's mags are always going on about investment buys yadda yadda." Another email arrives: "You've got to start thinking about how to work your makeover for less than designer prices. The thing about the shave is a case in point – it doesn't cost anything to do things right. You can stand up straight for free."

A free makeover appeals to my parsimonious sensibility. So instead of buying a new suit, I take my old one out of the wardrobe for the first time in years and find that the trousers only just about cover my croissant-thickened waist. The jacket fits well, though. Earlier, Allen had told me that the proper length for a jacket is dictated by the following: extend your arms downwards and cup your hands. The hands should just cup the bottom of the jacket. With this jacket, even my huge monkey arms can't reach that far.

I need to slim down pronto for the next step of my makeover, during which I plan to wear this suit for a sophisticated, pleasure-fixated gathering. But how? I am (perhaps insanely) taking as my text Kingsley Amis's book, Everyday Drinking. He writes: "The first, indeed the only requirement of a diet is that it should lose you weight without reducing your alcoholic intake by the smallest degree." For the King, food gets in the way of the real business which, insofar as I understand him, is the cultivation of hangovers. Hangovers are twofold. There is the physical hangover, whose chief remedy is the following: "Immediately on waking, tell yourself how lucky you are to be feeling so bloody awful." This is a very good point: it is akin to the one that set me out on this journey. If my problems are so superficial as these, then I shouldn't worry.

Then there is the metaphysical hangover for which Amis counsels reading the most gloomy verses of Milton, the grimmest bits of One Day in the Life of Ivan Denisovich and listening to the despairing bit at the end of the Pathétique symphony. All of which should cheer you up and put you in the mood for starting the process of drinking again. Yay!

This, to be sure, is man's diet. I put myself on it before heading to Cognac in western France for the final stage of my makeover. Yes, I could have visited a cocktail waiter and got him to show me how to make Mad Men martinis. But my quest is for European sophistication. Cocktail waiters have always seemed risible style gurus anyway, ever since Tom Cruise played one.

"Have you ever kissed a tree?" Marc Boissonnet asks me as we settle back in the Château de Bagnolet in Cognac to sip our aperitifs. Beyond the terrace, the English-style garden descends into the mist that is overhanging the river Charente at dusk. Nobody said becoming a man would be this tough. "This cognac is aged in such a way that everything points towards a strong, masculine character, utterly sophisticated, spicy fruit matched perfectly with woody notes that connect you with nature. Can you not taste the bark? It is as though you're wrapping your arms around a tree trunk."

Boissonnet is giving me remedial lessons on how to drink. "How do you drink in England?" Exclusively to excess, I reply. It is an existential quest for oblivion. We drink not for pleasure but to escape ourselves. "Then," says Boissonnet, "you must stop and do what Talleyrand suggested."

Charles de Talleyrand-Périgord was an enduring French diplomat of the 18th and 19th centuries who once reprimanded an English visitor for gulping down a glass of cognac. "The first thing you should do," explained Talleyrand, "is take your glass in the palms of your hands and warm it. Then shake it gently, with a circular movement, so that the liquid's perfume is released. Then, raise the glass to the nose and breathe deeply." "And then, my lord?" his visitor asked. "And then, sir," continued Talleyrand, "you replace the glass on the table and talk about it." But, the visitor didn't reply, how will that get me drunk?

Very French. And not very Mad Men. In Mad Men, however sophisticated the cocktails get, however much Don and Roger get down to 2am manly confidences at chic Manhattan bars, the booze is instrumental and the pleasure that it gives is never extended by talking about it. By contrast, Frenchmen like Marc Boissonnet take their pleasures seriously. We spend the next few hours talking over dinner about wine, terroir, provenance. Only when I tell Boissonnet that our digestif reminds me of rain falling on a nighttime roundabout in West Bromwich does he conclude proceedings.

The following day, after a hard morning's tasting, we adjourn to the bar for a pre-lunch aperitif. I feel elegant in my suit, suave in my newfound appreciation of wine, admitted to a secret world of sophistication that always seemed to be beyond me. I now know why I have come to this corner of France: it is the denouement of a drama where I have become a different, a better man.

And then doubts muscle in. Isn't there something unmanly about enjoying dressing well, in trying to become cultivated and taking one's pleasures seriously? I look across to Graham the photographer, who seems comfortable enough in his fleece. No doubt, I think, I'm going to come across in these photos like bald mutton dressed as gigot d'agneau, like a try-hard who should not have ideas above his station. There's a nagging sense that I have got the whole thing wrong, that I don't belong here, that, ultimately, I am and always will be an impostor. Clearly, my makeover isn't yet complete.

This article was amended on 10 January 2011. The article should make have made clear that the trip to France for both the reporter and the photographer was paid for by Hennessy, which owns Chateau de Bagnolet.