“Whenever people discuss timelessness in fashion, the debate is often framed as a battle between classic tailoring and fleeting trends,” Die! Workwear’s Derek Guy writes. But that’s not the whole story. “Navy blazers and penny loafers may be classic, but they won’t become true wardrobe staples unless they resonate with you.”

Likewise, the latest trend might not sit well with you, either. And that’s OK. “Without the ability to rise above trends, personal style becomes impossible.”

If one item of clothing best defines the current era of menswear, it’s wide trousers. While this can be daunting for those of us who lived through the skinny-jeans era, there are cheat codes, as the menswear journalist Ashley Ogawa Clarke informs us.

“Wider pants often look best when their proportion is balanced out with a smaller item on top,” he writes. “Known as the ‘big pants, little shirt’ look, it has become a go-to for trend-conscious guys over the last couple of years. It can be achieved by either downsizing to a fitted tank top or T-shirt if you’re cool with showing your body off. Or, for something on the safer side, a slightly cropped shirt, sweater or jacket.”

As for sneakers: “The most prevalent trend for 2025 will be low profile,” MR PORTER Buyer Sammy Skipper predicted at the start of the year. “It will transcend across every type of brand, from sportswear to designer.”

He certainly wasn’t wrong. But how to wear them? “These shoes were popular in the indie sleaze era,” Lauren Cochrane, senior fashion writer for The Guardian and author of The Ten, tells us. “I think you need to be a bit careful to avoid looking like a throwback. No skinny jeans – and probably not anything cropped. They would look nice with wide chinos or straight-leg jeans. It might be fun to have sport socks, or a more understated choice could work as a contrast.”

By the time you hit your forties, you should be “confident of the tools you have in your toolbox and your ability to use them”, the designer, art director and menswear consultant Aaron Levine tells us. “For the most part, I wear thoughtfully designed and well-made staples. Can’t go wrong. I try to do my best to eliminate the flash and the trash and just wear easy, comfortable things that allow me to feel like myself.”

“I’m a big believer in taking a shower, putting on something nice and going out for a proper meal or making a proper meal,” the actor Stanley Tucci tells us. “Otherwise, everything is just the same. And that’s the way we tend to dress these days. No matter where you go, you dress the same way unless you’re going to a wedding.”

So, don’t just compartmentalise your life. Compartmentalise your wardrobe to make the most of everything you do. (Or, at the very least, make Tucci happy.)

Spare a thought for the dads on the school run. You’ve got a child – maybe more – to get fed, dressed and at the classroom before you even think about what you’re going to wear to the office. Handily, we have a hack.

“A big swishy – and crucially, dark – winter coat is definitely your friend,” Johnny Davis, style director at Esquire UK, told us. “And a good way to distract from or cover any wardrobe shortcomings.” Noted.

Not all overcoats are made equal, however. For instance, do you know your balmacaan from your mackintosh? Both Scottish in origin, the former is “rooted in country living” while the latter is “its urban counterpart”, Derek Guy writes. “Not that you can’t wear either in both environments – traditional rules governing dress faded a long time ago – but their history shapes how we see them today. Whereas the balmacaan can be casual and rustic, the mac looks sleek and polished.”

There’s also the ulster and car coat to further muddy the water – plus, chesterfields, surtouts and wraprascals to get your head around. Thankfully, Guy’s guide covers all.

“The no-fail rule is to go by proportion,” Ilaria Urbinati, the stylist behind everyone from Barry Keoghan to Donald Glover, told us on the subject of timepieces. “Skinny suit, skinny lapel, thin watch. If you’re going for something big and bolder or a more casual look, you go for a rugged watch or a bigger watch. As you get to know your stuff, then you can play against those rules a little bit. It can be fun to have a sportier watch with a suit, but proportions are everything. You don’t want that tiny little Tank if the suit gets to be more American Psycho.”

The journalist and InStyle co-founder Hal Rubenstein offers his steer on a material he’s very familiar with: leather. “Leather doesn’t exactly give, certainly not at first,” he says as guidance for first-time wearers. “And while you’re not going to wear it to Bikram yoga, you need to adjust to more restricted movement. The jacket or coat should fit exactly at your shoulder break and come high up your armhole (it will give eventually). You should be able to bring your elbows parallel to your chest.”

Urbinati also has thoughts on leather jackets. “Go oversized and let [the jacket] fall almost like a slumped-on coat,” she says. “Then it has a more effortless look and looks less like Fonzie from Happy Days.”

As for what to wear with it: “I think if you throw it over a thin sweater or knit it does calm the whole look down, so it’s less like leather daddy,” she adds.

“Every generation discovers Ivy on its own and inevitably filters it through their own lens,” the menswear writer Eric Twardzik says on the resurgence of the preppy look. “As a millennial, I came up with late-2000s’ ‘neo-prep’. It was, in retrospect, a bit twee and certainly far too tight. I’ve enjoyed Gen Z finding Ivy on their own through a different aesthetic, which feels very informed by 1990s Polo and J.Crew – oversized fits and pleats.”

While the prep look is flexible enough to do it your own way, there are certain standards to maintain (not to mention the handbook to keep in mind). So, before breaking the rules, it pays to first learn them.

“The lynchpin of the whole aesthetic is an Oxford-cloth button-down with a soft, unlined collar whose points extend enough to create that fabled ‘roll’,” Twardzik says. “Drake’s does the finest version I’ve found. Beyond that, a good pair of beefroll penny loafers and higher-rise chinos or jeans. Now you’ve got the foundation.”

“The best thing about a cardigan is its versatility,” the stylist Gary Armstrong says. “You can wear it super easy, with jeans, relaxed and chic as a lighter layer for [between-season] dressing; or in place of a blazer for a twist on classic casual formality.”

Which isn’t to say you can wear one with anything – especially not worn with something “too bulky underneath”, Armstrong adds. “Perhaps avoid button-up shirts for comfort and a look that isn’t too forced.”

If in doubt, wear it like Paul Mescal, with a “vintage T-shirt, the more beaten up the better”.

In his guide to turtlenecks, the menswear blogger Henry Duffield ended on a power pairing that you might not have considered – this item of knitwear and a neatly trimmed beard.

“The turtleneck emphasises the wearer’s face because it naturally draws our attention upward,” he writes. “That is partly why the garment can be so flattering, but it also means your personal grooming regimen is going to come under the spotlight. It pays to stay shaved or keep the beard trimmed and to look after your skin and hair. It’s the best way to get the most out of your rollneck.”

What’s cooler than being cool? Not worrying about what is cool in the first place, it turns out. “Being cool means having the confidence to continue wearing something even if it’s no longer considered cool,” Derek Guy tells us. “You can still do this, so long as you know the historical language of dress.” (Consider MR PORTER your Duolingo.)

The biggest colour in menswear right now is also one of the most overlooked: brown. Done right, it can add richness to any outfit, looks good with most skin tones and slips into numerous style codes. And it particularly lends itself to tonal ensembles.

“Brown is a neutral colour,” says Michael Fisher, stylist to the likes of Jake Gyllenhaal and Sam Rockwell. “It’s found in nature and extremely versatile. All levels of brown, starting with tan into taupe, chocolate and bark, became popular again during the quiet-luxury movement. Layering in cream became the formula, down to the butter-soft sneakers and up to the cap.”

New research shows that the clothes we wear can have an impact on whether people trust us. As fashion psychologist Shakaila Forbes-Bell reports, it all comes down to a perception of self-control. Shaky outfits and – in particular – fast-fashion trends can put doubts in others’ minds.

“Fast fashion isn’t just about the way the clothes are produced,” Forbes-Bell writes. “It’s also indicative of the way they’re bought. We often forget that shopping and styling yourself are decisions, but they are. And most of us would trust a slow decision-maker over a rash one any day of the week.”

Her advice: take your time and dress like your authentic self.

“I’ve relearnt that all my pre-phone years’ routines are the ones that matter,” says Joshua Homme, frontman of the rock band Queens of the Stone Age. His top tip for staying grounded and present in the moment? Sewing. “I like to sew on the bus when I’m bored,” he shares. “Yeah, just sew things on.”

Which is great for sticking a bad-ass patch on a denim jacket. Plus, your mental health – if not “for the fingertips as you bounce around the planet”, Homme shares. But what about the bigger alterations that your wardrobe might demand? “The key is always a great tailor.”

“One of my forever reference points for wearing shirts in the summer is Matthew Perry in Friends,” the creative director and model Richard Biedul tells us. “From his Oxford button-downs to his Cuban- and revere-collared shirts, he maintained a strong sense of personal style.”

“To be sure, there are specific workplaces where you can wear shorts,” Derek Guys writes. “But you likely already know if you’re at one of those places (say, if you work in a store that only sells shorts). For all other situations, use common sense. If it’s something that you’d typically wear to the beach or the gym – open-toe sandals, stringer tank tops, stained tees – it’s probably not a good idea to wear them when you want to signal reliability and professionalism.”