As we get older, it gets harder to rebel. Spray painting anti-war slogans seems messy, you can’t really function without that morning cup of tax-dodging coffee, and your place of work sadly doesn’t include mohawks in its acceptable uniform policy.
So what’s the grown-up way – short of becoming a scientologist – to fight the establishment? Breaking style rules, of course. Flouting those now mouldy pieces of age-old ‘wisdom’ on how men should dress, and looking all the more stylish for it. It feels good to be bad.
1. Never Wear Navy And Black
Navy is great. Black is great. So it stands to reason that pairing the two is – haters take note – great. Like not wearing white after Labor Day (we’ll get to that in a bit), this is a rule that’s fast losing the relevance it once might have had.
That said, there is best practice when bolting these two darker hues together: the trick is in choosing pieces that complement, rather than compete with, one another. So swerve a midnight blue suit jacket with (very similar) smart black trousers and try a black roll neck with a navy pair instead.
The beauty of navy and black is its versatility; although they’re both colours traditionally associated with (and work exceptionally well for) eveningwear, they’re just as easily thrown together for an off-duty weekend look – think a navy polo shirt with black jeans and white trainers.
2. No Brown In Town
As if modern life wasn’t hard enough – we’re expected to hold down jobs, pay rent on time, not steal food from the office fridge – we also have to make sure we’re not wearing brown shoes in town or (the even stricter version) after 5pm. Why? What’s going to happen? We’re not Cinderella. We’re not going to turn in pumpkins. They’re shoes.
Sure, you could take to carrying around an extra pair of black lace-ups to change into at 4:59pm, or you could adopt the Italian way of living and just respond to prejudice with the word “sprezzatura“. You can’t wear those – “sprezzatura”. We have a dress code – “sprezzatura”. I was saving that tuna sub for lunch – “sprezzatura”.
We get that the rule derives from the strict division between brown and black as markers of casualness and formality. But things change. Just look at brown suits – a modern go-to that can look equally if not more stylish and put-together than bog-standard navy or black versions, when worn by the right man.
3. Don’t Wear Joggers Outside Of The Gym
Without athleisure, the world would be a lot less comfortable place. So to menswear purists, we say – in a Braveheart voice – “They can take our Vibram Five Fingers, but they will never take our joggers.”
Of course, there is a difference between effortless and not making an effort. When it comes to wearing sportswear staples of any kind outside of the gym (which if you hadn’t guessed, we endorse), there are a few rules to adhere to.
Much like wearing a hoodie under a blazer, the same pair can’t be worn for both, not least because of the smell. The cut of any joggers worn as part of an everyday look should be streamlined and come as close to tailored trousers as possible. Similarly, the colour should be neutral, and there should be minimal-to-no branding.
What you wear with them is also important, so to create balance sub the lifestyle runners for a pair of minimal sneakers or even Derby shoes.
4. Never Wear Hoodies With Tailoring
Once upon a time, the only place you’d have worn a hoodie under a blazer was on the way to juvenile court. Now, though, hoodies and tailoring is a key high-low trend that combines all the comfort of the ultimate casual wardrobe hero with tailoring’s instant sprucing-up effect. It’s athleisure in its purest form.
Just to be clear, we’re not suggesting you throw on a gym hoodie under a work suit – that’d get you lifted by the fashion police. But a fairly lightweight hoodie free of brash branding, cut from a premium material and in a colour that reads more smart than slouchy will ensure your outfit comes off sports luxe. As opposed to, you know, just sports.
As for the tailoring aspect: given the look’s contemporary leanings, a roomy tweed suit simply won’t make the cut. Keep things on the slimmer side with a well-fitting two-piece in black, grey or lighter neutral hues.
5. Never Wear T-Shirts With Suits
Like layering hoodies, breaking this rule only works with tailoring that leans casual. So don’t even think about pulling a fast one by sliding a T-shirt underneath a dinner jacket. Because you’ll just look like a tool.
Less is more here: you’re already making a statement by not wearing a shirt, so there’s no need to shout by adding in loud prints or blinding hues. To wit, we’d suggest a classic cotton crew neck shape in a tonal variant of the colour of the suit – e.g. a white T-shirt with a stone suit.
If the thought of a plain T-shirt is enough to put you to sleep, add some interest in the form of a classic Breton stripe. Try either of these options out one of those days you don’t have time to change a whole look before legging it from work to watering hole.
6. A Tie Always Needs A Suit Jacket
Perhaps the main reason for this rule’s existence is everyone’s (understandable) abject fear of looking like Moss from The IT Crowd. But you only have to look at pretty much any J.Crew campaign shot ever to understand just how surprisingly sharp a shirt and tie can look without a two-piece.
The secret is a solid outer layer – whether that’s a simple Harrington, leather jacket or a sizeable shawl collar cardigan. Wear it closed over a shirt and tie and revel in the satisfaction of looking sharp without the stuffiness of a suit jacket.
7. Never Wear Boots With A Suit
Disregarding this rule not only looks cool but is also practical – after all, there’s only so much a pair of brogues can be put through.
However, boots – particularly Chelsea, brogue and Derby shapes – retain all the dressiness of smart shoes but double down on element-deflecting, meaning you dress the part without risking frostbite.
Try rugged leather lace-up styles with a tweed suit when off-duty or swap out office-ready Oxfords for a pair of black or brown Chelsea boots for a workwear change that won’t get your boss’ finger wagging.
8. No White After Labor Day
Not wearing a certain colour after a specific day of the year is probably the most absurd, outdated fashion rule of them all. Especially when you consider that the federal holiday observed only in America falls on the first Monday of September. Thanks to global warming, that period is still pretty balmy. So if you want to sweat your balls off in all black, be our guest. If not, this is probably one to file away with the history books.
Some may point to the calendar and explain that Labor Day also marks the official end of summer and therefore white should rightly be stowed away. To which we point to the white T-shirt, Oxford shirt, sneakers and even white jeans, which are a stylish choice whether worn pristine or roughed up.
9. Always Accessorise Modestly
Sometimes more is more. Equal parts bold and bohemian, heavily accessorised looks have been bowling their way through the runways in recent seasons, with combinations of brash Western-style belt buckles, fedoras, lightweight scarves and big sunglasses reverberating a rock ‘n’ roll spirit. And don’t let the fact that you can’t play an instrument put you off, most modern musicians can’t either.
If you only think of Mr T when it comes to layering men’s jewellery (and we pity the fool that does), then rest assured there are ways of doing this to look more Johnny Depp in Marrakech than Miami disco bouncer.
Try combining brown and black leather cuffs and bracelets together, or pile on plain silver bands, signet rings and subtle chains. But, whatever you do, don’t mix your metals. Because you’re not a fortune teller.
10. Don’t Wear White Socks
One part 1980s teen movie underdog, one part skate brand-obsessed hypebeast: menswear’s current predilection for white sports socks is, we’d wager, a reaction against those ‘kooky’ coloured and patterned sorts beloved by bankers intent on letting you know they’re about more than just business.
While they won’t pair well with every look (and definitely not a suit), white socks can make your casual get-ups pop. Try them with some Vans and a pair of cropped or pinrolled jeans for a mature take on skatewear. Just avoid wearing them with shorts, unless you’re actually 16 and working on landing your first kickflip.
11. Don’t Clash Patterns
It would take far too long to list the number brands and designers that have put this archaic rule to bed. From streetwear names to high-end labels, a no-holds-barred approach to pattern has resulted in the stylish splicing of everything from bright florals and paisley to camo and stripes. None of it should work, but it does.
If you’ve got the confidence to try it out for yourself, just remember that a razor-sharp cut is the difference between looking kaleidoscopically cool and channelling bag ladies.
However, if punchy prints aren’t your thing, then perhaps it’s a simpler mix for you. Try teaming a gingham tie with a striped shirt, or a tie and blazer in different checks, for a subtler pattern clash.