How To Dress Well: 15 Tips For Better Men’s Style
— Updated on 20 November 2023

How To Dress Well: 15 Tips For Better Men’s Style

— Updated on 20 November 2023
Randy Lai
WORDS BY
Randy Lai

Usually, our instructional fashion articles tend to focus on dress codes: an area of men’s clothing that varies wildly in importance, depending on professional setting and how much of a stickler you are for protocol.

To supplement, we thought it’d be a grand idea to broaden the discussion, compiling a set of rules — or guidelines, rather — that will help the man, who already knows how to dress well in black tie and cocktail attire, with vaguer quandaries about personal style.

how to dress well men
Image Credit: James Harvey-Kelly // pjt.com

How do you colour-match similar tones? What’s the difference between a ‘big’ fit and one that’s just plain baggy? Why does a well-made pair of sunglasses have the ability to elevate even the most basic outfit?

That isn’t to say that our advice doesn’t extend to the specific garments you should invest in on your journey to better dressing. But crucially, the most helpful takeaways all encourage critical thinking about men’s style. Yes, you heard right: we’re encouraging you to think critically about clothes. Exciting times…

RELATED: 14 Life Lessons From The Iconic & Inimitable Tom Ford



1. Fit Is King

An aspect of great men’s style that is consistently obsessed over and difficult to master, fit is the primary element in any outfit that most bystanders are most aware of — above branding, cloth, and even colour.

Fortunately, developing a basic understanding of how things should fit isn’t terribly difficult; yet once you get past the (mostly intuitive) rules that are governed by individual physique, little subtleties abound.

By extension, always remember it’s better to buy the less expensive of two garments and put what you’ve saved towards a great alterationist. This is conventional wisdom that works particularly well in the realm of tailoring, no matter whether you prefer slimmer or more voluminous proportions.

2. Learn The ‘Rules’ Before Breaking Them

This is advice that’s pretty self-explanatory.

It’s one thing to subtly deconstruct some of the aspects of formal attire that no longer reflect how we live, work, and socialise in the 21st century; yet quite another to show up at a close friend’s wedding reception in flip-flops. The former implies a nuanced approach, and an acknowledgement of what flatters you.

To pilfer the adage of a certain Swiss watch brand: “To break the rules, you must first master them”.

3. Develop An Eye For Cut, Colour, & Proportion

Closely related to our #1 rule (i.e. “Fit is king”), it’s similarly important to hone your eye for cut, colour, and proportion — all constituent parts that, together, build the foundation for great personal style.

Given that clothing doesn’t exist in a vacuum, it’s impossible to proscribe a cheat sheet for how to nail each one of these elements in turn.

What we will say though, is that you can learn a lot simply by being visually inspired: whether that’s through a vibey Instagram moodboard or the medium of Hollywood & world cinema.

4. Make Time For Maintenance

how to dress well men
Pictured: Daniel Day-Lewis, as the incredibly fastidious protagonist Reynolds Woodcock, in Phantom Thread (2017)

Another kernel of advice that pairs wonderfully with our other tips about how to dress well, making the time to look after your clothes is an act that, in the long run, will prove hugely beneficial.

In the interest of cultivating good habits, we recommend the following:

  • Clean and polish your leather shoes fortnightly (ideally more often).
  • Iron dress shirts, and store them on hangers.
  • Use a garment brush to dislodge loose dust and dirt on your suits/jackets after every wear.
  • Invest in a basic sneaker cleaning kit — especially for rare drops and discontinued colourways.
  • Do not send your kit off to the dry cleaners more than three times a year. An aggressive chemical process, dry cleaning tends to shorten the lifespan of tailoring and, in an ideal world, should be a once-per-year affair.

5. Buy Less, Buy Better

A deliciously ironic takeaway — especially for a website where we spend our days obsessing about new cars, drams, and watches — it’s still helpful to consider the concept of ‘buy less, buy better’.

Within this maxim, there are a number of ideas worth unpacking. In no particular order: buying fewer pieces of clothing over a given period is an effective way to promote sustainability; and, ideally, requires one to exercise more intellectual discipline.

How’s that exactly? If you’re only adding new gear to your wardrobe once or twice per year, then by dint of that infrequency, you’re more likely to think rigorously about each purchase. Having more to spend certainly helps that exercise.

6. Finesse Your Uniform

This one’s more of a suggestion than it is dogma.

For many people, evolving one’s personal style just isn’t a priority: justifiably low on the totem pole next to matters of work, health, and family. If that sounds familiar, you can still dress well (particularly from Monday to Friday) using the framework of a ‘uniform’.

A strategy that has been successfully adopted by everybody from service workers to billionaire oligarchs, it’s helpful to broadly sort out what clothes work well for you in day-to-day life and then pad that assortment so you can wear it year-round.

For some, the uniform will involve a sportcoat and neatly tailored trousers. For others, sneakers and sportswear. So long as it’s comfy gear you can rotate through during the week and put together without thinking about it too consciously, then you’ll be on the right track.

7. Look After Yourself (And Not Just Your Clothes)

The phrase mens sana in corpore sano (“a healthy mind in a healthy body”), attributed to the Roman poet Juvenal, comes to mind.

It’d be madness to spend thousands of dollars on custom clothing or a complete wardrobe overhaul, if just a few years later, you’re no longer in the physical condition needed to wear all the stuff you’ve spent so much time and money accumulating.

Consequently, getting sufficient exercise and acknowledging the nuances in your own body shape are as important as an encyclopedic knowledge of fabrics. If you can have both, why choose?

8. Avoid The Urge To Accessorise (Watches Excepted)

Pictured (left to right): The Vacheron Constantin Historiques 1921 and Patek Philippe Calatrava (Ref. 5227G) are both excellent distillations of the archetypal dress watch.

In contemporary fashion, the discourse has clearly trended back toward a healthy appreciation for men’s jewellery. But if you’re a bit of a classicist, or enmeshed in a vocation where it’s important to practice aesthetic restraint, we can safely say that nobody will begrudge you a classic mechanical wristwatch.

Again, as with almost everything in the realm of personal style, what form your watch takes comes down to what works best individually.

For the median Boss Hunting reader, we’d be comfortable recommending the ubiquitous (but still very flattering) steel sports watch. That said, if funds allow — and you’re not against a bit of weapons-grade nerdery — the “two watch” rule isn’t a bad one to start with.

Rather than needing to consolidate every desirable feature into a single watch (e.g. a date window, automatic winding, luminescent numerals), having two to work with unlocks a range of possibilities.

In Australia, many enthusiasts tend to favour a weekday/weekend split: roughly corresponding to the idea of a dressier, elegant design; plus something you can wear into the sun and surf.

9. Buy The Two Best ‘Essential’ Suits Your Budget Will Allow

This is yet another guideline that is at its most relevant for those who enjoy/are already accustomed to a tailored wardrobe.

In essence, by buying two suits in fairly neutral shades of colour (e.g. greys and navies) you’re able to maximize the number of ways in which they can be worn — mixing, matching, and even wearing the trousers as casual separates.

To do this well, we’d recommend a cloth woven with a bit of texture. In a setting like Australia or New Zealand, high-twist wools like fresco work especially well. Woven with a unique arrangement of crisscrossing yarns, frescos are distinguished by their crisp, dry handle and superior resistance to creases.

Value For Money Recommendation: Suitsupply, M.J. Bale
Luxury Recommendation: Ring Jacket, Brioni
Made-To-Measure Recommendation: Trunk Tailors, REMY

10. Don’t Skimp On Shoes

how to dress well men

Like many of the essential ingredients in a classic men’s wardrobe, leather dress shoes are at their best after they’ve been gently worn in, polished, and patinated with repeat use.

In order to approach the “ageing gracefully” stage, however, it’s crucial you purchase leather shoes that, at a bare minimum, are made with natural vegetable-tanned leather and a Goodyear welt construction. We’d recommend a budget of at least $600 to be on the safe side.

As to the specifics of style, a lace-up brogue or oxford always works well for the suit-and-tie brigade. But for those who’ve embraced wearing tailoring casually, the classic penny loafer — good in calfskin, but even better in suede — is arguably the most versatile option. If your needs lie somewhere in the middle, Chelsea boots in the style of R.M. Williams’ iconic Craftsman are an excellent compromise.

11. Embrace Excellent Eyewear

Our sentiments about eyewear are very easily located in one of the many quotable nuggets from Sir Winston Churchill.

“My tastes are simple: I am easily satisfied with the best.”

The epitome of a small article that punches above its weight, we’d go so far as to call eyewear an essential part of how to dress well — especially going into summer. That’s a sentiment shared by a huge chunk of the public: evident in the fact that, in 2023, you can find aviators that cost in excess of $1,000.

Having said that, there are a wealth of brands offering a product that is reasonably well-made at a palatable price point. For a few BH-approved options, Sun Buddies and Randolph Engineering both come highly recommended.

12. Find The Perfect Pair Of Jeans

Image Credit: 3Sixteen

Not to belabour the obvious, but a great pair of jeans is far and away one of the best investments men can make when versatility is the endgame for their wardrobe.

Previously, we’ve canvassed over a dozen of the best men’s denim brands on the market. Familiarity with product aside, it’s similarly helpful to think about how the cut and wash of your favourite jeans interact with what’s already in your wardrobe.

As a basic starting point, a classic straight-cut tends to offer the most versatility. In line with the iconic Levi’s 501, hallmarks of this style include a high rise; more room through the seat of the trouser; and a slight taper below the knee.

13. Invest In An Immaculate Sweater

Pictured: Actor Chris Evans, wearing a traditional cable-knit Árann jumper, in Knives Out (2019)

Very much a piece of seasonal advice. Nevertheless, there are few articles in men’s fashion that harness as much sensorial joy as knitwear.

Over the years, menswear nerds have written a lot about the unrivalled beauty of cashmere (and in turn, the brands who specialize in this noble fibre) but you needn’t necessarily fork out thousands of dollars in order to experience great knitwear.

Japanese high street brands, including the likes of Uniqlo, do great work for a very fair price; while M.J. Bale’s “Single Source” range furthers the cause of carbon neutral, Tasmanian wool like nobody’s business.

Rollnecks and shawl lapel cardigans all possess merit, but if you’re after that one essential piece of knitwear then look no further than the humble crewneck. A compact layer that can be worn interstitially, or gathered loosely about the shoulders, it’s much more flexible than you’d initially think.

14. Own, Don’t Rent, Your Dinner Suit

Pictured: John Rhys-Davies and Pierce Brosnan, in the NBC miniseries Noble House (1988)

Read sans context, we’re aware of how insufferable this might sound.

To be clear: if you’re in a position where there is neither any inclination nor financial incentive to invest in a decent dinner suit, one could see why renting would be attractive.

On the other hand, we’re willing to bet that you (along with a large chunk of BH‘s beloved readership) have the right occasion to really lean into elegant formal dressing at least twice a year. Think weddings, Christmas bashes, and the odd charity gala.

That being the case, having your own dinner suit handy is a real game-changer; offering, in tandem, a great incentive to stick to rule #7 — staying at fighting weight.

15. Say Howdy To Headwear

A good year-round recommendation, the humble hat (whether it’s of the cap or brimmed variety) is your not-so-secret weapon when it comes to injecting a dose of personality into any outfit.

While brimmed hats are a pretty tricky, context-sensitive article — which carry the devastating possibility of turning you into this guy — baseball caps (a.k.a. the ‘dad’ cap) are a pervasive element in contemporary men’s fashion. We have Succession and compelling neo-prep brands like Drakes and Aimé Leon Dore to thank for that.

Truthfully, however, the appeal is easy to understand. Simon Crompton, the renowned men’s clothing journalist sums it up thusly:

“A baseball cap worn with fine clothing appeals because of the contrast. Here’s a piece of sportswear being worn with something that [isn’t] sportswear. One’s fine and sharp, the other (ideally) worn and battered. It’s a species of high/low dressing.”


If you’ve enjoyed this article about the (lifelong) art form of how to dress well, then consider taking a moment to peruse some of our other men’s style features below:

Randy Lai
WORDS by
Following 6 years in the trenches covering consumer luxury across East Asia, Randy joins Boss Hunting as the team's Commercial Editor. His work has been featured in A Collected Man, M.J. Bale, Soho Home, and the BurdaLuxury portfolio of lifestyle media titles. An ardent watch enthusiast, boozehound and sometimes-menswear dork, drop Randy a line at [email protected].

TAGS

Share the article