There are almost too many considerations to list when it comes to the alchemy of finding the perfect shirt. Not only does the fit have to be perfect but it needs to sync with so many other details of your look, from the width of your tie to the style of your suit and the occasion for which you’re dressing.

To ensure your cuff matches your collar and much more, we enlisted the help of three menswear insiders. Button it while they dispense their advice

7) Getting The Right Fit:

How your shirt fits can have a big impact on your finished look, says Evan Drucker, director of menswear and accessories at Jaeger. It’s the the difference between a smart, precise silhouette and billowing shapelessness. “One of the constant mistakes men make is to buy a traditional classic fit shirt when they should be wearing a slimmer fit. Look for a shirt that that skims your body but doesn’t create lots of excess fabric around the waistband. You must be able to move in it, but you don’t want to be tucking in lots of fabric all the time”

6) Know Your Collar Size:

It’s not just the fit that you need to consider. Getting the right collar size will mean that the tie you choose looks streamlined once you’ve knotted it in place and, more importantly, you’ll be comfortable. Sam Kershaw, buyer at Mr Porter, has a fail-safe technique for knowing your collar size. Once you’ve used a tape measure to measure the circumference of your neck, try on a style in the corresponding inch measurement. Then, Kershaw says, “you should be able to fit a forefinger in between your collar and your neck when the shirt is buttoned to the top.” Et voila.

5) Matching your tie with your shirt:

Once you’ve perfected the fit, make certain your shirt choice works with your suit and tie. Kershaw explains that there are three ways to go with the classic workplace combo. “A solid colour/ tonal shirt from brands like Charvet and Emma Willis tend to be best suited with a patterned tie or something more extravagant like a paisley. Otherwise, you can wear a strong patterned shirt with either a plain satin or grenadine tie from brands like Drake’s or one with a subtle stripe like those from our Kingsman collection. For a more casual look, pair a Thom Sweeney button down shirt with a Lanvin knitted tie.”

4) matching your shirt with your suit:

When it comes to making your shirts and suits match-up, it’s all about proportion. “If you’ve bought a contemporary suit with slender lapels and a lean cut then your shirt collar should be small and your tie should be slim,” says Kershaw. “7cm wide is perfect.” Look to styles like this by Thom Sweeney which is suitably modern but with the added flair of super-sharp points.

3) Broaden the collar:

Another way to experiment with the traditional collar silhouette without making your look informal is to go wide. Take inspiration from this Thomas Pink shirt with a wide cutaway collar which sweeps horizontally rather than the traditional downwards trajectory. It’s a nice touch to even out the proportions of suits with long, slim lapels.

2) Ironing Your Shirts:

While plenty of modern shirt options come in non-iron fabrics (check out M&S for a good selection) there’s a certain appeal to the crisp look and feel of a freshly ironed cotton shirt. If anyone knows how to get an immaculate finish, it’s Nicholas Worth, of luxury shirt makers Hawes and Curtis. Use his expert tricks to make short and effective work of your ironing pile.

Get the iron as hot as possible, this will give the best finish.
Iron the reverse of the collar first, then the collar, cuffs and sleeves before doing the main body.
Never let the iron onto the buttons.
When you’re finished put it on a hanger and do up the top button. Leave it to air for two hours for the fabric to rest. Don’t wear it straight away as it will crease again immediately.

1) Going Off-Kilter:

While the classic tailored shirt should always have a place in your wardrobe, there’s also a new category of shirting which bridges the gap between the traditionally formal and a more relaxed approach. Consider the Grandad collar shirt; it’s crisp and pristine white and can be buttoned right to the top for a super-smart look, yet a simple undone collar and un-tucked styling experiment would transform it into a more relaxed piece. An excellent consideration if you’re going travelling and multi-tasking options