Usually, our instructional fashion articles tend to focus on dress codes: an area of menโs clothing that varies wildly in importance, depending on professional setting and how much of a stickler you are for protocol.
To supplement, we thought itโd be a grand idea to broaden the discussion, compiling a set of rules โ or guidelines, rather โ 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 do you colour-match similar tones? Whatโs the difference between a โbigโ fit and one thatโs just plain baggy? Why does a well-made pair of sunglasses have the ability to elevate even the most basic outfit?
That isnโt to say that our advice doesnโt 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 menโs style. Yes, you heard right: weโre encouraging you to think critically about clothes. Exciting timesโฆ
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Fit Is King
An aspect of great menโs 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 โ above branding, cloth, and even colour.
Fortunately, developing a basic understanding of how things should fit isnโt terribly difficult; yet once you get past the (mostly intuitive) rules that are governed by individual physique, little subtleties abound.
By extension, always remember itโs better to buy the less expensive of two garments and put what youโve 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.
Learn The โRulesโ Before Breaking Them
This is advice thatโs pretty self-explanatory.
Itโs 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 friendโs 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: โTo break the rules, you must first master themโ.
Develop An Eye For Cut, Colour, & Proportion
Closely related to our #1 rule (i.e. โFit is kingโ), itโs similarly important to hone your eye for cut, colour, and proportion โ all constituent parts that, together, build the foundation for great personal style.
Given that clothing doesnโt exist in a vacuum, itโs 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 thatโs through a vibey Instagram moodboard or the medium of Hollywood & world cinema.
Make Time For Maintenance
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 โ 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.
Buy Less, Buy Better
A deliciously ironic takeaway โ especially for a website where we spend our days obsessing about new cars, drams, and watches โ itโs still helpful to consider the concept of โbuy less, buy betterโ.
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.
Howโs that exactly? If youโre only adding new gear to your wardrobe once or twice per year, then by dint of that infrequency, youโre more likely to think rigorously about each purchase. Having more to spend certainly helps that exercise.
Finesse Your Uniform
This oneโs more of a suggestion than it is dogma.
For many people, evolving oneโs personal style just isnโt 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 โuniformโ.
A strategy that has been successfully adopted by everybody from service workers to billionaire oligarchs, itโs 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 itโs comfy gear you can rotate through during the week and put together without thinking about it too consciously, then youโll be on the right track.
Look After Yourself (And Not Just Your Clothes)
The phrase mens sana in corpore sano (โa healthy mind in a healthy bodyโ), attributed to the Roman poet Juvenal, comes to mind.
Itโd be madness to spend thousands of dollars on custom clothing or a complete wardrobe overhaul, if just a few years later, youโre no longer in the physical condition needed to wear all the stuff youโve 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?
Avoid The Urge To Accessorise (Watches Excepted)
In contemporary fashion, the discourse has clearly trended back toward a healthy appreciation for menโs jewellery. But if youโre a bit of a classicist, or enmeshed in a vocation where itโs 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, weโd be comfortable recommending the ubiquitous (but still very flattering) steel sports watch. That said, if funds allow โ and youโre not against a bit of weapons-grade nerdery โ the โtwo watchโ rule isnโt 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.
Buy The Two Best โEssentialโ 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) youโre able to maximize the number of ways in which they can be worn โ mixing, matching, and even wearing the trousers as casual separates.
To do this well, weโd 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
Donโt Skimp On Shoes
Like many of the essential ingredients in a classic menโs wardrobe, leather dress shoes are at their best after theyโve been gently worn in, polished, and patinated with repeat use.
In order to approach the โageing gracefullyโ stage, however, itโs crucial you purchase leather shoes that, at a bare minimum, are made with natural vegetable-tanned leather and a Goodyear welt construction. Weโd 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 whoโve embraced wearing tailoring casually, the classic penny loafer โ good in calfskin, but even better in suede โ is arguably the most versatile option. If your needs lie somewhere in the middle, Chelsea boots in the style of R.M. Williamsโ iconic Craftsman are an excellent compromise.
Embrace Excellent Eyewear
Our sentiments about eyewear are very easily located in one of the many quotable nuggets from Sir Winston Churchill.
โMy tastes are simple: I am easily satisfied with the best.โ
The epitome of a small article that punches above its weight, weโd go so far as to call eyewear an essential part of how to dress well โ especially going into summer. Thatโs 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.
Find The Perfect Pair Of Jeans
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, weโve canvassed over a dozen of the best menโs denim brands on the market. Familiarity with product aside, itโs similarly helpful to think about how the cut and wash of your favourite jeans interact with whatโs already in your wardrobe.
As a basic starting point, a classic straight-cut tends to offer the most versatility. In line with the iconic Leviโs 501, hallmarks of this style include a high rise; more room through the seat of the trouser; and a slight taper below the knee.
Invest In An Immaculate Sweater
Very much a piece of seasonal advice. Nevertheless, there are few articles in menโs 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 neednโt 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. Baleโs โSingle Sourceโ range furthers the cause of carbon neutral, Tasmanian wool like nobodyโs business.
Rollnecks and shawl lapel cardigans all possess merit, but if youโre 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, itโs much more flexible than youโd initially think.
Own, Donโt Rent, Your Dinner Suit
Read sans context, weโre aware of how insufferable this might sound.
To be clear: if youโre 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, weโre willing to bet that you (along with a large chunk of BHโs 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 โ staying at fighting weight.
Say Howdy To Headwear
A good year-round recommendation, the humble hat (whether itโs 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 โ which carry the devastating possibility of turning you into this guy โ baseball caps (a.k.a. the โdadโ cap) are a pervasive element in contemporary menโs fashion. We have Succession and compelling neo-prep brands like Drakes and Aimรฉ Leon Dore to thank for that.
Truthfully, however, the appeal is easy to understand. Simon Crompton, the renowned menโs clothing journalist sums it up thusly:
โA baseball cap worn with fine clothing appeals because of the contrast. Hereโs a piece of sportswear being worn with something that [isnโt] sportswear. Oneโs fine and sharp, the other (ideally) worn and battered. Itโs a species of high/low dressing.โ
If youโve enjoyed this article about the (lifelong) art form of how to dress well, then consider taking a moment to peruse some of our other menโs style features below:
