I bought a jacket in Martin Margiela the other day. I know, I know. Hold the front page: magazine journalist buys expensive item of clothing. Still, it has been a long time since I made a serious fashion purchase. It’s not a particularly outré jacket. In fact, it’s rather plain, sombre even. Think edgy estate agent. Think mortgage adviser with attitude. Think unremarkable man in anonymous grey jacket. Still, sombre or not, it is by Margiela, a maverick design visionary from Antwerp. Whereas I’m a boring middle-class male from Shepherd’s Bush. You can see it’s a bit of a leap.

Really, I just wanted a jacket, and I had endured similar trials at Selfridges, Liberty and elsewhere – sombre grey jackets with an air of ineffable exclusivity being harder to come by than you might think.

It cost £695: not hedge-funder money, but not exactly Asda price, either. Not with the credit crunch round the corner (such are the considerations of a boring middle-class male from Shepherd’s Bush). I felt guilty for days afterwards. I kept thinking about all the sensible things I could have spent that money on. God, sometimes I even bore myself.

But men’s approach to shopping is very different to women’s. We shop reluctantly, cautiously, infrequently and alone. Ever the hunter-gatherers, we view shopping expeditions as precision-targeted surgical strikes. As for fashion, we men prefer “style”. We men judge clothes not just on their look or feel, but on their robustness.

Funny thing is, time was that I used to buy foolishly trendy clobber without a backwards glance. In my days as a teenage clubber, I thought nothing of blowing my student loan on a Jean Paul Gaultier T-shirt, Vivienne Westwood trousers or a jacket by Helmut Lang. I once bought a pair of boots that cost more than my car, and my wardrobe was crammed with Comme des Garçons, Yohji Yamamoto, Katharine Hamnett and Armani. I bought throwaway T-shirts from Sign of the Times, and hung about in style bars talking deconstruction with the manufactured boredom that only the truly fashionable can be bothered to cultivate. I fancied myself rotten.

Then all that stopped. I got a job, moved in with a girl, began to keep regular hours and spend money on items such as residents’ parking permits and house plants. All the money I had previously spent on drugs and Day-Glo Walter Van Beirendonck tank tops was being rather more prosaically allotted. Suddenly, high fashion seemed, well, gay. While I could appreciate the strict aesthetic of Jil Sander, the gaudy glamour of Dolce & Gabbana, the techno genius of Prada and the jet-set sexiness of Gucci, none of it was for me. I had grown up and grown out. I was a jeans and T-shirt man, another shapeless kidult in baggy denims and trainers.

Spookily, my retreat from fashion coincided with a similar movement in wider culture. The lad stereotype of the late 1990s was largely antifashion: he wore combat trousers, cagoules, sweatshirts and shoes that looked like cornish pasties. His style icons were the brothers Gallagher, men who looked better dressed for a hike in the Peak District than an evening of sybaritic carousing. Gone were the dandies and boulevardiers of the 1970s and 1980s. It was all about the superannuated modfather, Paul Weller, and his silly feathery hair.

But it has begun to change. Perhaps it started with the regeneration of Savile Row at the turn of the century, with Richard James and Kilgour grabbing slobbish Englishmen by their food-stained lapels and dragging them into a fantasy of sophisticated chic. Or maybe it was all those Shoreditch dandies in their skinny jeans, pointy shoes and too-tight tops, making us baggy older men feel out of touch and inspiring Hedi Slimane, then at Dior Homme, to refashion the male silhouette from slouchy to skinny.

In any event, a transformation is afoot: men like me, who, a few years ago, would have shuddered at the prospect of an afternoon browsing Bond Street’s emporia, have begun to come over all fashion-conscious. I have long had friends who wear Burberry and Dunhill, but I now know chaps who shop at Miu Miu, Dior Homme and Alexander McQueen, brands that are defined by their sartorial daring rather than understated classicism. The rise to prominence of the American tailor Thom Browne, whose suits are tight, short and unmistakably fashionable, is testament to the new mood of experimentation in menswear. The fact that Tom Ford, formerly of Gucci, has chosen to concentrate on menswear for his return to the rag trade tells its own story.

I spoke to a selection of men for this story: a couple very fashion-savvy, others less so. Philip, a solicitor, is 35. He dislikes the word “trendy”, but concedes he is fashion-conscious. He wears APC, Margaret Howell and younger British menswear labels such as Albam. “I’ve always been into fashion,” he says. “But when a new look such as the skinny thing comes along, it reinvigorates you. Even my mates who aren’t into fashion have started shopping.”

Philip also believes that, perhaps for the first time, the high street has started to play a role in how stylish British men dress. “Cos is brilliant, and I bought a great suit in Topman recently. I think the same thing that happened to women a few years back, when it became cool to shop in Topshop, is starting to happen to men. Because much as I’d love a Thom Browne suit, I can’t afford it.” And Dior? “That’s too much of a look for me,” he says.

Dior is not too extreme for Paul, an architect. At 28, he is an example of fashionable London manhood. I have known him for three years and have never seen him wearing anything other than the skinniest of skinny black jeans, the pointiest of pointy black shoes and the sharpest of sharp black jackets. He wears Marni and Westwood, Topman and H&M. His favourites are Dior – “clean, slim, modern” – and Raf Simons, another cutting-edge Belgian.

“I love shopping,” he says. “I love everything about it: the shiny rails of new clothes, the shops designed to look like something out of 2001: A Space Odyssey, the cute shop girls . . .” Best of all, though, is the “cathartic whoosh” from spending “silly money” on fripperies.

Paul thinks that most men’s fear of shopping stems from indecision and insecurity. “Give a City banker 10 minutes to work out his annual tax return without a calculator: no problem. Ask him to choose between blue plaid or plain white for a casual shirt: no chance. Men have trouble committing. We hate to make mistakes, so we agonise over choices. We consult our wives, worry about it; then, after all that, decide against buying it.”

Women, Paul feels, are more liberated when it comes to shopping: they will buy something on impulse and take it back if they don’t like it. “We need to take a leaf out of their book,” he says.

That said, even Paul concedes that most of us will never approach shopping as a pastime, as women do. I asked my friends if they could foresee a time when we would shop together, in the way that our wives and girlfriends do.

Mark put it best: “Frankly, Alex, I can’t think of anything worse than sitting in Selfridges watching you trying on clothes. That’s Saturday-afternoon purgatory.”

I couldn’t agree more.