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How to Buy a Shirt – Why Fit Is the All-Important Factor

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Section: Essential Men's Business Shirts - Blog

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Whether you buy your shirts off the rack or order them custom made, if they don't fit, you've wasted your money. If the fit's too loose, you look slovenly; if the fit's too tight, you look and feel uncomfortable. Here's our expert advice on how to get the perfect fit.

When it comes to buying a shirt these days, one size does not fit all. Regular, slim-fit, skinny, it’s almost as confusing as choosing from the Starbucks menu. So how do you buy the perfect shirt and does it really matter if it’s super-skinny or a baggy shouldered mess? You’ll be wearing your suit jacket anyway, right? Well, we have a few thoughts on the subject.

It’s all in the fit

While many factors play a role in your choice of shirt such as colour, fabric, and pattern, none are as important as the fit. Once you get this aspect right, the rest should fall into place.

A well-fitted shirt will complement your body shape either accentuating the good parts or hiding those that you’d rather not display to the world. Did someone say love handles? Once you achieve this, you will naturally feel more comfortable and therefore more confident.


But before you go off buying the loosest fitting shirt in the hopes that you can conceal your partiality for chocolate muffin breakfasts, bear this in mind. A loose shirt means large folds, and large folds make you look bigger; you can see where we’re going with this. Conversely, and some might say perversely, a too tight shirt will also make you look big, in fact, too big for your shirt.

So this is where a tailor’s expertise is worth its weight in solid gold buttons. A good tailor will find the middle ground that complements your physique perfectly no matter what size or shape you are.

But what if you’re in a hurry and an off the rack shirt is your only option?

You may find that choosing a fit is a confusing task as many off the rack brands opt for peculiar shirt categorizations. Who really knows what a super-duper-hosepipe-slim-fit shirt is anyway?

The fits

There are actually three main categories and although there are a variety of subcategories, every shirt known to man should fall into one of these three groups.

Classic/Regular fit

This is the shirt that your father wore to the office every day, the shirt that you wore to school, and most likely the first shirt that you ever purchased. The majority of shirts on hangers in menswear departments will fall into this category.

This is your failsafe.


You can’t go wrong with a regular fit shirt. The slightly generous use of fabric gives it a bit of a boxy look, but it also ensures ease of movement making it popular with men that favour comfort over style.

Slim Fit

If the regular fit takes first place in the popularity stakes by sheer force of numbers, then the slim fit shirt runs a close second. This style is much more prevalent in recent years as we men start to appreciate the nuances of style that help us stand out from the crowd.

A slim fit shirt has a higher armhole that allows for a shaped look that is closer to the body making it a prime choice for those with an eye for the sartorial.


However, its moniker does not mean that it is made exclusively for less than portly individuals. Even those of us packing an extra kilo or two can pull off this style once it’s not too tight or if the fabric used has a little elasticity to it.

Skinny Fit

The Skinny fit shirt does exactly what it says on the label. This is an ultra-tight-fitting shirt that hugs every inch of your torso. Every muscle, every bulge is there for all to see. Needless to say, this isn’t the most popular choice in the average male population.


Unless you are incredibly self-confident and have a particular body shape that looks remarkably good in extremely tight-fitting clothes, then we would give this one a miss.

Which fit should I choose?

When off the rack is the only option we would choose either regular or slim fit shirts and shy away from the skinny fit.

Heavier set men should feel more comfortable in regular fit shirts while those with a lighter build or with more of a focus on style should opt for a slim fit.


However, if you have the time we highly recommend having your shirts tailor made as no two men are the same. A wide neck doesn’t necessarily mean wide shoulders and popping into your friendly neighbourhood tailor – that’s us here at Montagio – will make sure that your shirt fits snugly in all the right places while leaving room for movement.

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We tailor make mens suits, jackets and shirts for all occasions. Each garment is custom designed, precisely made-to-measure and is guaranteed to fit you perfectly. Unlike others, we offer you end-to-end service and a personalised styling session where we take the time to understand your needs to ensure you get the colour, style and fit you want.

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Named in GQ Magazine's "Best Tailors" list, and the highest reviewed tailor on Google, Montagio has paved the way for discerning men to get suited up with style. We offer a truly personalised experience, specialising in custom designed, perfectly fitted suits, shirts, coats, and shoes for for business, weddings, formal and casual events. Our showrooms are visually packed with designs that inspire plus thousands of fabric options, making it easy for you to get the look you want. Our expert stylists will advise and professionally fit you and frankly won’t let you walk out until we’ve tailored your perfect garment. Since 2010, we have custom tailored looks for thousands of happy customers. To experience the same red-carpet service, book your personal appointment today.

Simon Frazer

Montagio did a great job on wedding suits for me and my two groomsmen. Bally provided us with fantastic service and the result was definitely superior to an off-the-rack option... more »

Kiran Dosanjh

I have bought a total of 11 pieces custom made so far - quality and attention to detail is spectacular, material choice is broad and the input customers have in creating the exact look they want is a great experience... more »

Roy Soliman

I went back for another suit, a few shirts and some ties. Outstanding! I had so many complements on my new suit yesterday! more »

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