Search for some form of men’s style how-to on Google or YouTube and you’ll get at least a few results saying something like this:

Five Style Rules You MUST FOLLOW.
Men’s Style Mistakes You’re Making RIGHT NOW! (Don’t Do #3!!!).
Cardinal Sins of Men’s Style.

And so on, and so on, and so on.
The communities populating some of these sites and video comment sections are so mired in a prison of rules-based thinking when it comes to how you wear your clothing, it’s sometimes even more pitiable than having no clue at all.
I suppose it’s somewhat a pathological reaction; you realise you’ve been clueless about something for years, then when you finally see some of the light, you beat yourself up about your past and become a bit of a zealot in the process.
Many of these types will see another light at some point, and realise that it’s OK to have fun with your style, and that your style should be your own.
Many others will voluntarily stay in style rule prison.

I see the body as a canvas, with clothing being the brush you use to paint a unique picture on that canvas, every single day.
It’s part art, part science, and without one, the other can suffer.
Once you’ve got the science nailed, the art needs to be honed, otherwise things don’t progress past the stage of robotic and repetitive movements.
Go forth with only the art, however, and it becomes art for art’s sake.
Which isn’t necessarily a bad thing, however it is what constitutes modern art.
A field that sparks adoration from one, and pure disdain from the next.

Moving on, here are six style ‘rules’ that belong in the prison cell’s bins.

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Don’t wear more than one collar

I’ve heard this one spouted a few times, and I’m tackling it because it seems to be one of the last entrenched bastions in the minds of people who have otherwise escaped from the pit.
Somewhere along the line, somebody said you can’t wear a collared sweater over a collared shirt.
Which would mean no rugby tops over shirts or ties.
Tell that to the prep/Ivy crowd and they’ll first laugh, and then show you how doing two collars can look fantastic.

On a technical level, I find this ‘rule’ to be strangely hypocritical.
It’s only ever directed at sweaters.
However, even hardened supporters of this rule tend to wear a shirt jacket over a casual shirt or polo for a clean casual outfit.
On the other side of the line, you have the men brave enough to wear a turtleneck over their collared shirt, with the shirt collar popped to show the tips poking through the neck.
I’ve not done it, but I admire how some gents make it look. I’ll give it a shot at some point.

Don’t tuck your polo shirts or tees in

Another strange one, and this one definitely has to have originated within the last two decades, because tucking all forms of shirting in has been the standard move for many decades before that.
It’s especially important to tuck your tees and polos when wearing them with tailored pants, or just if you have a higher rise trouser.

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If you head to my Instagram profile and see my ‘following’ list, you’ll see a plethora of stylish men who tuck in their tees and polos.
The ‘rule’ against it, quite simply, is naff.

No ties with button down collars

Another bizarre one I’ve seen perpetuated lately.
American style has been characterised by the button down collar since its heyday, so there’s no way that ties and button down collars should be separated.
They’re a match made in heaven, especially if the collar is devoid of fusible, with little to no interlining and a generous length to facilitate a lovely collar roll.

A button down collar might look a little at odds with a particularly smart silk tie, like a wedding tie, but it’s a great match for knitted ties and repp stripes.
Something the Americans, and Ivy Style practitioners across the world have been doing since kingdom come.

Everything has to be form fitting, and jackets must be short

This one has sprung up through people following the trend of slim-fit suiting started by Thom Browne and other designers in 2010.
A few educators in this space have latched onto those designs and treated them as God, deriding anyone who chooses something more classic. Their disciples are often outspoken with matching opinions.
Thankfully, there are also educators and influential figures who combat this myth.
A good source of information on classical proportions and how to play with proportion in order to best flatter your body is Alan Flusser’s book Dressing The Man, which I’ve previously reviewed.

You must wear a pocket square with a tie

Though pocket squares as a current menswear trend are past their heyday, and I’ve certainly moved on from them for the most part, I often see the odd person in the comment section of any one of my friends on Insta questioning ‘no pocket square?’ like a mortal sin has been committed.
I personally dislike that pocket squares cause an asymmetrical bulge in my left lapel if I wear them, so I avoid it.
Other people have different reasons for not wearing one.
Many others have their own reasons for always wearing one.
Square or no square, is a matter of personal taste and choice.

Jeans must be worn with a belt

This goes for any pair of pants with belt loops, but I most often see it disputed with jeans.
Many are taught that simply because the space for a belt is there, that it must be filled.
I wear a belt in one of two circumstances:

a) I think it brings something to the outfit (often a Western style belt fits this bill).
b) my trouser waist isn’t correctly fitted and I need a belt to keep my pants from being around my ankles.

If I think a belt is going to ruin the flow of an outfit, the belt stays on the hanger. If that means I have to change my pants, then it’s time to take those pants to an alterationist anyway.

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