Our style expert answers your most pressing questions.

This week Mr Steve Bannon (formerly President Donald Trump’s closest advisor and the man memorably described by late-night host Mr Stephen Colbert as “the handsomest guy at the liquor store”) once again made an egregious sartorial error – and therefore headlines – by wearing two collared shirts at the same time. This is the wrong kind of overshirting. Below, we deal with the right kind of overshirting – ie, the perfect item to see you through the transition from summer to autumn.

Also this week, we help a schoolboy out with a school uniform question, and decide whether or not it is OK to wear cufflinks with knitwear.

As ever, you can submit questions directly via email to dan.rookwood@mrporter.com or via our social media channels.

What is the best way to wear an overshirt? And any recommendations for a first purchase?

From Mr Todd Fisher, via email

The overshirt is a garment some people insist on calling a “shacket” (a portmanteau of shirt and jacket) and it is a particularly handy and easily stashable go-to at this in-between time of year when the weather can’t quite make up its mind what season it is. Worn untucked, it functions as a practical lightweight jacket or as an insulating layer under a coat. You can unbutton/unzip it when hot or do it up when cold.

MR PORTER currently has 38 overshirts on the site in various different styles, 21 shirt-jackets, and seven of near cousin the chore jacket.

The overshirt has its origins as a fatigue shirt, a piece of military workwear – and this is evident in this patch pocket khaki number from Aspesi, this olive green one from Folk, or this army shirt from AMIRI.

There are some denim-type examples such as this cotton canvas piece from Chimala or this from Paul Smith.

Then there is a lighter-weight shirt which draws on that trend for wearing pyjamas outside the house. Consider this brushed flannel shirt from Our Legacy or this loungewear shirt from Oliver Spencer.

Or you could channel the urban outdoorsman stylings of this red checked Ami lumberjack overshirt or this one from Filson.

They can be worn unbuttoned or unzipped over a T-shirt, or buttoned up like a coat, depending on the temperature. But my favourite way to wear them is just to fasten the top two buttons and leave the rest unbuttoned.

My school uniform is a black blazer and trousers with a white shirt. However in the sixth form (final two years of high school), we have the freedom of wearing any coloured shirts we like. What colour shirts would you therefore recommend to complement a black uniform? The tie is black and red and silver.

From Mr Cameron Rosie, via email

The temptation when you’re suddenly free to do something that has hitherto been forbidden – drive a car, drink alcohol, break free of strict school uniform – is to go a bit mad, at least at first. Which is understandable, but not advisable.

In this instance, you still have some limiting parameters – namely the colour of your uniform, but more so the colour and pattern of your school tie. This is obviously not what you want to hear but I’m afraid your best option remains a white shirt. While the price is probably prohibitive for a sixth-former, this classic Thom Browne button-down would be perfect, given the colour co-ordinating grosgrain striped placket which would poke through visibly if you had your tie schoolboy-ishly askew.

But of course you want to exercise your sixth form privilege. So I would suggest (brace yourself): grey. This would work well with the black and silver of the tie and not clash with the red stripe. Either plain grey, or with a little texture such as a button-down chambray, or perhaps with a small-scale pattern, such as a thin stripe or check. The scale of the pattern must not compete with that of the tie. For example, this Prince of Wales check Tom Ford shirt may be too busy when worn with the school tie.

Disclaimer: the following suggestions include some expensive shirts, more for the purposes of general demonstration than specific recommendation. There are more important things to spend your money on right now. Like your first car.

Mr Tom Ford, a staunch advocate of black suiting, offers both a formal and a casual grey shirt options. Consider also the style of these shirts from Canali, Prada and Engineered Garments.

If you have some different options when it comes to your tie (e.g. a prefect’s tie or sports colours tie or house tie), then this will open up more flexibility in shirt choices. For example, I rather like the effect of a pastel shirt when worn with a black suit and a black tie – consider light pink, mint green, light purple. This helps to off-set the funereal black. Mr Jude Law sported this look rather well in the otherwise forgettable 2004 remake of Alfie.

Is it acceptable to wear a jumper/pullover over a double-cuffed shirt? If so, where should the jumper cuff sit on the shirt cuff? If not, is it blazers only?

From Mr Edward Tritton Halls, via email

How old are you, Mr Halls? For a man of more advanced years, I’d say wearing a double-cuffed shirt with knitwear is rather elegant. On a younger man (under 35), it might look like a little “sloaney”. But you could soften the impact by wearing those knotted fabric cufflinks you can buy in gentleman’s outfitters, or a more fun pair of metal cufflinks such as these, these or these from Paul Smith.

As for where the jumper cuff should sit on the shirt cuff, I would position it similarly to the length of a blazer sleeve – so you’ll be showing about half an inch to an inch of shirt cuff. Does this mean exposing the cufflinks? Yes, just preferably not ostentatiously so.

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