The gap between tailoring and workwear is narrowing – here’s how to navigate the trend in style.

How does tailoring respond to a style landscape that’s now more relaxed and much less uptight than it once was? How do you dress up when you’ve grown used to the practicality of workwear and the comfort of sportswear? Nowadays, men expect to feel comfortable, and for more and more of us, tailored clothes are optional, which means that while we’re still happy to dress up for an occasion, most likely a wedding, the idea of wearing a stiff suit on a daily basis doesn’t fill us with unalloyed joy.

We’ve reached this point because, by and large, convenience wins. But let’s pause for a second. Convenience is all well and good, but sometimes you need to take the time to make the effort.

The good news is that in 2018 a man can look smart without dressing up in a wedding suit day in, day out. If you’re looking for low-maintenance tailoring, then be assured that the new season’s clothes want to meet you halfway. There are loads of options for guys who like the practical advantages of workwear and the relaxed feel of sportswear, but also want to smarten up.

Five years ago, the blueprint for contemporary tailoring involved tight clothes fussily decorated with collar pins, tie clips and pocket squares. These days, the mood and the silhouette are more relaxed, even among the most ardent fans of the tailor’s art. At the twice-yearly menswear trade show Pitti Uomo in Florence, the guys normally sport more adornments than a Christmas tree, but at the most recent show it was hard to find a man in a tie. This year’s big trend was to wear a Hawaiian shirt under a softly tailored jacket, whereas only two years ago a man wearing a T-shirt under his suit jacket might have been asked if he was on his way to a Miami Vice party. Now he looks like he’s found a sweet spot between comfort and style, and let’s remember that it’s impossible to seem stylish if you’re not comfortable.

So what are these new clothes like? Utility means different things to different people, but the Italian label Z Zegna now offers a 100 per cent wool suit that can be laundered in the washing machine at home. This is a first for high-end tailored clothes, which have always presented a maintenance challenge because they’re normally dry-clean only, even though dry-cleaning doesn’t do them any favours because few laundries know how to press a jacket. The Z Zegna suit takes the form of a classic navy two-piece, which is about as versatile a garment as it’s possible to own. Worn over a plain white T-shirt and with white canvas sneakers, it is relaxed and relevant, a point subtly reinforced by the patch pockets on the jacket. It can also be dressed up if necessary.

Meanwhile, our own label, Mr P., offers a navy blazer with soft shoulders. Removing the padding from the shoulders and chest of a jacket transforms the experience of wearing it by making it seem and feel much more relaxed. For an even more chilled version of the same, look no further than Brioni’s wool and cashmere blazer, which looks like a softly tailored garment but feels like a particularly luxurious cardigan. It’s as soft on the inside as it is on the outside and again has patch pockets that are useful for both travel documents and for discreetly signalling the jacket’s informality. Other brands offering sophisticated tailoring with a casual feel include New York label Noah and Japan’s Camoshita. One of the most stylish exponents of this strand of informality is Spanish designer Mr Carlos Castillo, creative director of Man 1924. The brand’s Kennedy jacket is a modern piece of tailoring, but it owes more to the rumpled tweed jackets worn by working men in the 1930s than it does to any aristocratic preference.

There’s more to tailoring than just jackets, and one of the things that’s hard to come back from is the comfort of sweatpants. Any man who’s got used to wearing trousers with a drawstring waist is going to take a while to readjust to a fixed waistband and a leather belt. While he acclimatises, he might like to try a pair of Barena’s trousers, which combine sober, work-appropriate fabrics and colours with the feel of pyjamas. Another useful source of clothes that are as comfortable as pyjamas is the brand P. Johnson. Maybe it’s the label’s Australian roots, but whatever the reason, the clothes live up to their promise of “lightness, simplicity and wearability”. The look is relaxed, the feel is informal, but the image is sophisticated, even when the clothes blur the lines between tailoring and workwear, as with the patch-pocket overshirts that double as soft jackets.

Being well-dressed means adjusting to changes in society, and even formal clothes should reflect the simple, incontrovertible fact that casual clothes are having their moment in the sun. That said, utility in tailoring doesn’t just mean machine-washable jackets with enough pockets to swallow the contents of your belt bag, useful as these things are. It also means the professional, social and romantic benefits that you accrue from looking stylish. The good news is that, no matter what the occasion, you can now look good and feel good at the same time.