Can good style be taught? Probably not: in general, the best dressers make sartorial decisions that would sound shockingly bad on paper. And it would be a pretty boring state of affairs if dressing well came down to following a set of prescribed instructions.

What can be learnt, though, are the principles on which good dressing is based. These are the foundations for thinking about your own self-presentation, and a toolkit with which to approach the sometimes-overwhelming prospect of looking for new clothes. Of course, from there, you can be free to colour outside the lines.

Much of that thinking comes from years spent working within menswear. So, we called upon some of our most hardened style experts, from stylists to editors and writers (and, of course, a few of MR PORTER’s own staffers). Here’s what they came up with.

It’s worth figuring out what, and who, you’re dressing for. “For me it’s always been about getting dressed for yourself, not for Instagram and not for other people you think you’re going to run into,” says Mr Lawrence Schlossman, co-host of the menswear podcast Throwing Fits. “It’s all about putting together an outfit to start your day that gives you confidence, that makes you feel good about yourself and that gets the day started on the right foot. As the great [American football coach] Deion Sanders said, ‘look good, feel good, play good.’”

MR PORTER’s Style Director Mr Olie Arnold recommends limiting the number of options you’re considering for your outfit. “Having a couple of options is fine, but no more than three,” he says. “Then spend no more than 10 minutes making the final decision. Nine times out of 10, it will be the first one you put on. Trust your instincts.”

“The adage ‘wear the clothes, don’t let them wear you’ is the simplest but most important piece of advice,” Arnold says. “When you’re not comfortable, your body language will say so and your outfit will bomb.” That comes down to choosing pieces that feel relevant to you, rather than shoehorning yourself into a brand or trend that doesn’t click with your own style.

The coolest piece of menswear isn’t going to help you if it doesn’t sit right on your body. “Know thyself in a very literal sense, how you’re built and how you’re shaped,” Schlossman says. Having this information means you can work out what looks good and why. For Schlossman, it’s all about getting to grips with his “really long legs and super short torso,” which determines the cuts and proportions he chooses (and if you’re not sure how, MR PORTER has an extensive archive of articles on the subject).

Rome wasn’t built in a day. Neither should your wardrobe. “A good wardrobe should be slowly built over the course of five or 10 years,” says the menswear expert and proprietor of Die, Workwear!, Mr Derek Guy. That might not be much help when you have an event next week. But focus on steadily adding one or two good pieces at a time, rather than going on TikTok influencer-style hauls. “You shouldn’t expect to acquire everything at once,” Guy says. “And if you buy fewer things, you can justify spending a little more on each item.”

Ms Lili Göksenin, Senior Editor at MR PORTER, advocates a Ms Marie Kondo-esque approach to shopping. “When you’re shopping, take a beat to ask whether it’s something that really speaks to you, and if you can see yourself wearing it for years to come,” she says. “Sleep on it, if you need to. If it still makes you feel good, then get it.”

Learn about who makes the very best versions of the things you like to wear – even if you can’t afford them right away. “Sticking to a beautiful, best-in-class piece and conscientiously working towards it is a great feeling,” says menswear writer Mr Finlay Renwick. “It helps you to appreciate it more.” It might take longer, but it’ll mean you’re building up an arsenal of top-tier menswear pieces that will last. “I can’t afford a pair of J.M. Weston shoes at the moment,” Renwick says. “But by November… I still probably won’t. But at least I will have tried.”

Stylist Ms Felicity Kay is an advocate of buying better clothing, with a focus on the quality of the pieces. “When I say better, I don’t necessarily mean more expensive,” she says. “Look at where things are made and the fabrics they are made from.” Clothes made in countries with a heritage in craftsmanship (such as the UK, US, Italy or India) are likely to sit better on your frame.

Clothes that have been crammed into overstuffed wardrobes are likely to stretch, meaning they’ll sit poorly on your body. Make the time to keep things properly organised. “Don’t hang knitwear or T-shirts,” Kay says. “Hang your jeans or trousers instead to make room in your drawers for any clothes that should be stored flat.” And if you can’t get everything in neatly, it’s time to sell or donate a few pieces.

No one wants their clothes to be skin-tight or clinging in all the wrong places, and going up a size is an easy way to get a better fit. “Consider switching to looser cuts, which tend to be more flattering and usually have a slimming effect,” says MR PORTER’s Content Director Mr Rob Nowill. “And remember, no one will know what’s written on the size tag except you.”

Shoes are important, so get them right. As Mr Chris Amfo says, “shoe contact is often made before eye contact, so be sure to make a good impression.” Build up a rotation of four to five pairs of good-quality footwear: an elevated sneaker, a leather hard-soled lace-up, a Chelsea boot, a classic loafer, and a pair of more technical sneakers would be a good place to start.

Accessories are key, and sunglasses are an obvious place to start. “I think that all of my problems might be solved with a pair of Jacques Marie Mage sunglasses with little tinted lenses,” Renwick says. The right pair will bring definition to your face and instantly make your outfit look more considered. Make sure to choose the right pair for your face shape.

“A lot of people who are starting to get into style start with fun, loud sneakers or loafers,” Schlossman says. “It’s a gateway for people to step into the wider world of personal style. If that is your entry point, then work out what pants have the best pant-shoe interaction with those shoes, and then work your way up, putting it together from there.”

We shouldn’t have to say this in 2024, but your trousers shouldn’t be puddling around your shoes. “It’s probably the mistake I see more often than any other,” Göksenin says. “And it’s the fastest way to make you look like an amateur.” Read up, and get them taken up.

It’s nice to have new things, but aim to find a balance between novelty and old familiars. “It’s hard to look authentically well-dressed if everything you’re wearing is fresh-out-the-box new,” Nowill says. “It’s why the Kardashians never really look stylish. Allow your clothes to develop some signs of wear – they’ll hang on your body in much more flattering ways and allow you to truly inhabit them.”

Learning to layer unlocks a whole new realm of dressing. You can wear even more clothes at any one time, and pieces take on different characteristics depending on what they’re worn with. “Layering is a skill that can be learnt,” Renwick says. “It doesn’t require you to spend a fortune, it will make you look considered and tasteful, and it prevents you from being freezing cold for six months of the year.” Not sure where to begin? Here are the six pieces you should start with.

“Stick to the two Ps: planning and preparation,” Arnold says. He recommends thinking about your outfit a good four hours before you need to get dressed. Better yet, lay something out the night before and enjoy another 15 minutes in bed instead of a panicked gaze into your wardrobe.

Some of the big brands are big for a reason: often, they’re genuinely the best at what they do. But don’t overlook smaller labels that can bring an element of the unexpected. “Look for off-the-beaten-path independent brands,” Nowill says. “They can bring some curveball elements to your wardrobe and get people asking, ‘Where in the world did you get that from?’”

Adding things to your Wish List is a quick and easy way of making your own personal mood board. “Patterns and personal trends will start to form of the things you love,” Arnold says. “Plus, it makes it easier to make decisions when you need to add to your collection.”

The secret weapon to almost every stylish man we know? A smattering of pieces from Japanese menswear brands. “A lot of guys worry that those labels might be too avant-garde for them,” Nowill says. “But their collections are chock-full of quirky, characterful pieces that will bring personality and individuality to the stuff you already own.” If you’re not sure where to start, check out MR PORTER’s edit.

Inspiration comes from all places, including the older generation. Talking about a recent trip to Paris, Renwick recalls the effortless style of men over 60. “You could tell these guys had really lived in their clothes and use them for function,” he says. “The style is secondary, but even more effective for that reason.”

Everyone needs a “thing” and that applies to clothing as well. “A couple of consistent elements in your day-to-day outfits will give you a recognisable identifier and help you to develop a stronger sense of your own taste,” Nowill says. “Maybe it’s a couple of pieces of jewellery that you never take off. Maybe it’s a colour. Maybe you’re the ‘jazzy sock guy’. Find it and stick to it.”

If you’re wearing a statement piece – maybe it’s your shoes, or a great shirt – allow that to take centre stage. “If I’m wearing a great pair of cowboy boots, I’m not going to wear some crazy loud pants and a crazy loud knit and a huge statement coat,” Schlossman says. “I’m going to try and highlight one thing.”

A few carefully chosen pieces will make you look like a more confident dresser. Maybe that’s a single statement ring, or a necklace with sentimental value. “Don’t underestimate its appeal,” Nowill says. “Remember the hysteria around Connell’s chain?”

It’s all too easy to over accessorise, weighing you down with unnecessary gewgaws. “Accessorising is tricky and should be done with care,” says How Long Gone co-host and GQ columnist Mr Chris Black. “When in doubt, take one thing off.”

Chances are, some of your clothes will need tweaking so that they fit just right. It’s worth doing some research into your tailor and finding one you can trust. This is going to be an important relationship. “A few inches here and there make all the difference to the cut and comfort,” Amfo says. “So, get on first names with someone who can bring out the best in your silhouettes.” If you don’t know where to start, check out our guide to finding one.

Don’t be tempted to toss out your clothes at the first sign of holes. “Getting things fixed isn’t just better for the planet,” Goksenin says. “It adds character and charm to your clothes.” And it means that perfectly worn-in pair of jeans gets a longer shelf-life. If you’re based in the UK, consider MR PORTER’s FIT & FIX service.

Black’s advice for logos is short and simple: “Save them for the gym. The era of being a billboard is over.” Instead, look for more subtle brand signatures, such as Bottega Veneta’s discreet triangle tabs, or LOEWE’s cursive motifs. These will gesture to your awareness of the designers you love without screaming about them.

You probably only wear a blazer on one of the rare occasions you wear a suit nowadays, but they are much more versatile than they first appear. “Keep a few handy,” Black says. “They work for any situation.” As a starting point, look to a sports jacket in a softer colour that you can throw over jeans, alongside a sharper cut in black or navy to wear in the evening. And, for the love of God, make sure you’ve cut the vents.

No one wants to get the dress code wrong, but it’s always better to have made _too _much of an effort. If such a thing even exists. “I’ve never regretted being the smartest person in the room,” Nowill says. “But I did regret the time I turned up to a black-tie dinner in a slogan T-shirt.”

As well as being more sustainable, a focus on natural fibres also benefits how your clothes will look. “When it comes to knitwear, coats or tailoring, I always check the materials before buying,” Kay says. “Knitwear, for example, with a higher proportion of natural materials over synthetic blends, is always going to look better for longer.”

For Kay, there are a couple of tips that guarantee a longer life for your favourite clothes. “Never tumble dry, buy a good debobbler for knitwear, and get shoes resoled before you wear them through – not after.”

Getting dressed should be something you take pleasure in. So, lighten up and wear what makes you happy. After all, it’s just clothes.