From shop to catwalk, the search for something to wear leaves Shane Hegarty bewildered. But help is at hand

As a man ages he is faced with some deep sartorial questions. When is it no longer appropriate for him to wear distressed jeans? Are slogans on T-shirts strictly for twentysomethings? Should belts move closer towards your nipples with every year? There was a time when even teenage boys dressed like they were old men. No longer. Men have been thrown deep into the fashion well, and face similar crises to their womenfolk. As they hit their 30s and beyond, they don't want to dress like their fathers, but they don't want to look like they've just taken up skateboarding either. Yet, this is exactly the moment when shopping becomes an increasingly stressful activity.

Faced with the trial of visiting shops in which every item of clothing looks like it has first been put through a thresher, and is sold by an insolent, spiky-haired shop assistant who's not interested in shouting over the banging techno, shopping becomes a dispiriting experience. With dwindling patience, men often give in to the awful temptation to let someone else buy their clothes for them. Far too early, a man's fashionable period consists of a short window of independence, between the childhood years when his mother bought his clothes for him and middle-age onwards, relying on his wife to get him a new jumper for his birthday and some socks at Christmas.

For me, the moment of crisis came during the sales when a simple search for a pair of jeans led to a tedious misadventure. Having bought a pair of jeans on the recommendation of the shop assistant (Me: "Are these a regular fit?" Assistant: "Yes"), it was only when I took them home that I realised that they were so baggy they could double as tall ship sails. Returning to the shop, the assistant promised again that they were a regular fit. "Well," he clarified, "they're as regular as they get in this shop." As it was a sale item, I could only swap it for something else. This is a standard retail practice of which, I later discovered, all women have an innate understanding, but it led to several lost hours of trying to find an item of clothing that wasn't either ripped, torn, shredded, dishevelled or severely distraught.

Apparently, it's not an unusual scenario for men who have reached a certain age. "You see so many guys out and about in town and they look lost. They haven't a notion and they need help," says Marietta Doran, a stylist and personal shopper. "It has become very intimidating, especially when they don't know what's out there."

The increasing worldliness of Irish men allows them to observe - and envy - the style of men in Italy and Spain, and for them to want to look just as good. Sometimes, it can backfire.

"There's a white shirt craze at the moment," says Doran. "A lot of men go overseas and they see that look, maybe with linen trousers and boat shoes, and they think they'll look good with that at home, but they overdo it. It only works in the Med."

There are some tips older Irish men could pick up from our European neighbours. Grooming, she says, is key. Men should stay properly shaven, and get a decent hair cut and use cosmetics with the confidence of an Italian. The shoes, she adds, are vital too. Italian boots cum shoes are good, because they show a sign of maturity, but with accompanying trendiness.

H&M and River Island have some mature clothes alongside the funkier stuff, she says. And she recommends a bit of advanced research, such as checking websites or buying some magazines. But aren't the catwalk photos always ridiculous? They usually feature chiselled young men flouncing down the ramp while wearing a flapping selection of outré clothes that would earn you only a slagging in the pub and ensure that your children would never want to be seen in public with you again.

"Yes, but you could always wear some part of it," she says, and points out that male models tend to be somewhat more mature than female models, so there are plenty of role models in the magazines. And Irish men mightn't look like Brad Pitt or George Clooney, but they can always find something to borrow from their styles.

However, the relaxed setting of the modern workplace poses added problems for men. Without the safety of just sticking a suit on everyday, it can be hard to know what is acceptable. Are T-shirts okay? What about jeans? Or runners? Being a common conundrum, there's plenty of advice on the web.

"Men should look around at their peers and clients," says one article, "and then try to dress better than everyone else. If you're uncertain of your own taste, pick someone in your company who is a really sharp dresser. Tell him, 'Let me take you to lunch at a nice restaurant, then come with me to Saks and help me pick out some clothes'." That sounds like every guy's dream lunchbreak.

When it comes to the office, Doran believes, jeans should be kept for weekends. And tracksuits are an absolute no-no. "And runners, oh my God!" I point out that, in my office, it hasn't been unknown for people to turn up for work in shorts. "I can't believe that," she gasps. "My God, if that's the effort you're going make with your appearance, then why not just wear a dressing gown all weekend?" Bang goes Tony Soprano's status as a style icon.

"Most men don't really shop for leisure, but shop when they need to shop," says Ann Finn, head of menswear at Brown Thomas. "For women it's a leisure pursuit. There was a university study recently that said that for men it's a Neolithic thing, they feel most comfortable where there is water, trees and somewhere to hide. They like to come in and get advice, it can't be a prolonged thing. Some don't even come in, they just phone the shop."

She offers the heartening thought that there are plenty of 19-year-olds who can't get away with distressed jeans any more than a 39-year-old can. "It really depends on your personality." Extroverts can get away with things no matter what their age, she says. If you're a little more conservative, you should dress that way. There is a caveat, though. "I hate to say it, but the body shape changes from about 30, and off-the-peg clothes don't fit so well. They need to buy better labels, because they have a better cut." As they age, men often retreat to one or two familiar stores, and lose any sense of adventure they once had. Often they settle into the predictable brands such as Ralph Lauren or Hugo Boss.

It doesn't have to be that way, insists Alan Kelly, owner of Gentlemen Please, whose shops in Blackrock and Glasthule in Dublin have earned a reputation for rescuing style-conscious men who have become more distressed than their jeans.

"It's about the job and lifestyle, and it is obviously about physical shape too. But there are no barriers really, and personality is what dictates style," says Kelly. "Some guys will come in [ and] because they're a big guy have heard they should only wear stripes. We take everyone as we see them. Some guys in their early 30s look older and might stick with a classical or conservative look, but then there are some in their early 40s who look in good shape and will look great with a nice plain T-shirt and a John Smedley jumper."

Last year, velvet jackets were a big seller among men of all ages, and Kelly says there are plenty excellent jeans for older men, even if they can be pricey. He has sourced plenty of labels to suit men who are flailing in the high street. "My biggest gripe is that the bigger stores are not trying to break barriers. They'll have two or three brands for a season, and the big stores are sticking to the safe. These are the people who call themselves the top of the menswear fashions, but they are not pushing themselves beyond their limitations of what's safe for them and their customers."

There is hope, so, for men who feel 30 years older every time they enter a high street store. A man can age stylishly, rather than drifting into middle age while buying shirts purely on the basis that they don't require ironing. The future, it turns out, doesn't have to involve trousers with elasticated waists.

Five to take to heart

Be yourself: buy clothes based on your personality and shape, not just on your age.

Keep it simple: a simple T-shirt and V-neck jumper works for a lot of older men, such as Brad Pitt. You mightn't look like him, but you can dress like him.

Tailor made: a tailored suit is always a winner, even without a tie. It works for George Clooney, anyway.

Ask and receive: men shouldn't be afraid to do a little advanced research or to ask for advice in the shops.

Don't get too ambitious: Bertie Ahern's yellow suit set a new standard for older men whose fashion radar is on the blink.

- Points to ponder

Five to take off

Hawaiian shirts: "No! I lived in New Zealand for a while, and it was acceptable there, but not in Ireland."

Three-quarter pants: "No! I can't stand them on guys. The problem is that they are usually accompanied by socks with runners. That's hideous."

T-shirts with slogans: "Absolutely awful."

Leaving shirt tails loose: "Not for anyone over the age of 25."

Bellies: "A jacket is always good over a shirt, rather than jumpers stretched over the belly."

- Stylist Marietta Doran's advice