THIS is How Clothes Should Fit a Man

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This post assumes that you’re looking for a general (but VERY useful) overview of how clothes should fit a man.

If I’m wrong, and you’re looking for the fit of specific garments, no stress – check out this grid below for links to individual fit guides that I’ve written.

So let’s get into it… We all know that our clothes should fit properly – but how should clothes fit a man?

Unfortunately, understanding, and actually getting, a proper fit is quite a nuanced and difficult job, and one that a lot of people, even those who really put in the effort, get wrong.

Clothes should fit comfortably on the body, with no pressure points, and look good and appropriate for that specific garment. They should be loose enough for the fabric to drape well, but can fit tighter or looser based on the wearer’s preference, and current trends.

The rest of this article will elaborate on how clothes should fit a man through a useful framework, which you can use when shopping to find clothes that fit, and with your own wardrobe to ascertain if the clothes you already have fit properly.

Before we start…

For a complete overview of the topic of finding clothes that fit in general (rather than just understanding how they should fit, which will help you find clothes, which is this article), I’d highly advise to also check out my epic companion article.

Framework for How Clothes Should Fit a Man

The framework states that, for a good, masculine, fit, any piece of clothing should be:

1. Good looking.
2. Comfortable
3. Looking like it should.

This is the best way of explaining clothing fit, as general advice such as ‘the garment shouldn’t be too tight or too loose’ is too vague, and isn’t always applicable, as we’ll see.

The next few sections will explain this framework, and how you can use it, in detail.

CLOTHING FIT POINT 1: ‘A clothing piece is good looking’

Ask yourself: ‘does the garment look good in every respect, from all angles?’ For example, for a jacket:

• Does the torso look good, or too baggy or tight?
• Does the body length look correct, or too short or long?
• Does the sleeve length look correct, or too short or long?
• Does the fabric drape correctly? (IMPORTANT)
• Is this the case for all angles, when you look side on, bend over, sit down, or do other day-to-day movements?

You may be wondering how you’ll know some of the answers to the above questions.

Personally, I don’t believe you have to have an encyclopaedic knowledge of, or experience with, clothing to know if something looks good.

As humans, we’re tuned to pick up on aesthetically well balanced and proportioned things, so when something looks ‘off’, you’ll likely notice it. Total absence of these pointers usually suggests that a piece ‘looks good’.

The most important thing here is that you actually care and pay attention to your clothes ‘looking good’, as you’re less likely to detect it if you’re not consciously looking for it.

Assessing ‘Drape’

I feel the drape of the fabric is an essential part of a piece of clothing ‘looking good’, and ‘looking masculine’.

A garment that is too tight will have too little fabric, and will follow the contours of your body too closely. This can accentuate your body type, making slim and average body types look less formidable, and put together.

If you’re in better shape, I feel you can get away with clothing with less fabric that hugs your contours closer, as your natural stature is more formidable. However, whenever I see this, it generally looks too tight, and would look better if there was more room for the fabric to naturally fall down – your masculine proportions would still be evident, but they would be less comically emphasised.

Conversely, a garment that is too loose will have too much fabric, and will completely swallow the contours of your body, making anyone look sloppy.

Unfortunately, drape is one of the more abstract measures of a good fit, so to help you assess the ‘drape’ of a garment, I introduce to you a trick I call ‘The Drape Guarantee’.

Essentially, for a garment to have a good drape, when worn, the drape should create:

• Clean, straight, unbroken lines, OR;
• Clean straight unbroken lines AND clean curved lines

Generally, if the drape is either of the above, it will elongate your stature, and look visually appealing.

Achieving Drape

To help you find garments that drape well, drape is usually affected by:

• The amount of excess material on a garment (as aforementioned)
• The type of fabric used for a garment.

Pieces with more excess fabric tend to produce more ‘circular lines’ than tighter garments (if they have a waistband that hugs your body), and pieces with heavier, thicker fabrics tend to create more elegant drapes that adhere to the above rules, compared to garments with thinner fabrics.

Because of this, getting a good drape on some items can be really, really hard.

Even myself, someone who pays way too much attention to these things, sometimes really needs to look hard to find certain items, such as jeans and t-shirts, that drape well.

This is because jeans and t-shirts are usually made of fabrics that (often cotton, and potentially some stretch in there), unless they have perfects cuts, naturally enjoy hugging the skin (even if there’s room), and wrinkling unaesthetically. On top of this, they’re usually not super heavy, so don’t have the benefit of being pulled down by gravity.

Consequently, I’m ultra vigilant when I’m trying on items in these categories, and like to refer more closely to specific ‘how should x fit’ articles for these pieces (though, you’ll still be fine with this 3-point system, and SUPER FINE if you combine both). In many cases, I compromise with an item that drapes 80% correctly, because it’s just so hard to get something that fits spot on.

Alternatively, you can look for options in other fabrics (such as Reiss’ t-shirts, which are 100% polyester, and drape super well).

Good drape is easier to achieve with things such as jackets, coats, and formal pants, which are typically made from materials that drape better, such as wool, and are heavier, so fall harder.

Example of ‘Good Looking’ Clothes Fit

As an example of the idea of being ‘good looking’, the ‘Extra Small’ (XS) sweater has an awkward drape in the torso, and I feel the sleeves are slightly too short, which doesn’t look great.

In contrast, the ‘Small’ (S) jumper drapes better in the torso, with a curved drape, and crucially, has longer sleeves, which looks better – as everything about this garment looks good, I would consider this sweater to ‘look good’.

However, depending on your taste (mine is evolving, you see), you may consider the ‘S’ jumper to be a bit short in length, and tight around the arms. In this case, this would not ‘look good’ to you, and still be a tiny bit on the tight side.

Responding to Point 1

When You’re Looking to Add New Clothes

• If it hits all of the markers for ‘looking good’, you can move on to step two.
• If the answers to any of the markers are that the garment is ‘too tight’, then try on the next size up, and start your evaluation again.
• If the answers to any of the markers are that the garment is ‘too loose’, then try on the next size down, and start your evaluation again.

When You’re Looking to Cleanse Your Wardrobe

• If there’s a problem with any of the pointers, you may want to look towards selling or donating that item, OR taking it to the tailor to get adjusted.

CLOTHING FIT POINT 2: ‘A clothing piece’s fit is comfortable’

Ask yourself: ‘is the fit of the clothing unequivocally comfortable, in all positions?’

• If the garment has any pressure points or sources of discomfort, it has a bad fit.
• If the garment restricts your movement in any way, it also has a bad fit.
• Is this the case when you do day-to-day movements, such as bend over, sit down, kneel, or twist?

Warning on Comfort

You have to be careful – and I’m speaking from my own experience – because it’s very easy to get mesmerised by an item that hits step one by looking so good, that you excuse it being uncomfortable.

For example, a couple of years ago, I bought this sports coat. At the time, I thought it looked incredible, which led to me excusing the fact that it’s clearly too tight for me (doesn’t help that I’ve put on weight since…)

Example of ‘Comfortable’ Clothes Fit

Specifically, the sports coat is restrictive around the shoulders, which provides a source of discomfort – I should have left it.

However, this sports coat is entirely comfortable and has no pressure points, so I was right to pick it up.

Annoyingly, despite the latter jacket being more comfortable than the former, they are the same size, 36″ – make sure you read my companion article for an elaboration of this super important point.

But overall, ignoring the comfort level of your clothes is a sure-fire way to hate their fit.

Responding to Point 2

When You’re Looking to Add New Clothes

• If the piece has no sources of discomfort, you can move on to point three.
• If there’s any source of discomfort, try sizing up, and start your evaluation again.
• If no sizes are comfortable, leave it; there’s nothing wrong with not buying something if no sizes work for you.

When You’re Looking to Cleanse Your Wardrobe

• If it’s not comfortable, you could consider selling or donating the item.

CLOTHING FIT POINT 3: ‘A clothing piece is looking like it should’

Finally, ask yourself: ‘does the fit of the piece look like it should, from all angles?’

For example, in my opinion:

• It’s most appropriate to have a suit have the appearance of being tailored closely to your body, with little excess fabric, and;
• It’s most appropriate to have a sweatshirt have the appearance of having a more generous and looser fit.

Example of Clothing ‘Looking Like it Should’

We can apply this to specific cases, like this linen shit, which, according to a lot of sources, doesn’t ‘fit properly’ – I could probably fit 3-4 fists in this chest area.

But, again, in my opinion, the looser fit of this shirt is appropriate and ‘looks like it should’, because it’s a lightweight casual linen shirt, that’s short enough to be worn untucked.

Responding to Point 3

As guidance, next time you’re out shopping, keep the following in mind:

1. What fit would suit this style best? Slim, or looser?
2. How does this piece look on me? Slim, or looser?

When You’re Looking to Add New Clothes

• If the answers to the above questions are the same, the piece looks like it should, and you can purchase that item.
• If the piece looks too tight for its style, try sizing up, and start your evaluation again.
• If the piece looks too loose for its style, try sizing down, and start your evaluation again.
• If no sizes look like they should, you should leave it. If the issue is that it’s too large, you could purchase it with the intention of taking it to the tailor. (Not always recommended, as any changes may compromise point one – ‘looking good’)

When You’re Looking to Cleanse Your Wardrobe

• If the piece doesn’t look appropriate on you, look to sell/donate that item OR take it to the tailor to get adjusted, to make it fit closer to the expected look.

Recap of The Clothing Fit Framework

• If it hits all 3 points – a piece looks good, is comfortable, and looks like it should – the piece fits correctly, and you can add it to your wardrobe!
• If it doesn’t look good – size up if it’s too small, or down if it’s too large.
• If it’s uncomfortable – size up for extra room.
• If it doesn’t look like it should, again – size up if it’s too tight, or down if it’s too baggy.
• If you change size, start the evaluation again.
• If none of the sizes hit all 3 points, leave it! (or be brave, and take an overly baggy item to a tailor)

Example of Good Clothing Fit

Understanding, and getting an evaluation right with the framework is super important, so let’s look at one complete example of our old friend, my yellow jumpers.

• Let’s say we start with size XS.
• Step 1: I have to evaluate my ‘starting point’, size ‘extra small’, in terms of ‘looking good’.
  • The ‘extra small’ jumper doesn’t look good, as the sleeves are too short. As it’s too small, I size up to a size ‘Small’
  • This size small looks good now, so I move on to step 2, comfort.
• Step 2: This jumper feels very comfortable, and there’s no pressure points anywhere, so I move on to step 3, ‘looking like it should’.
• Step 3: For a jumper, I feel this looks appropriate.
• So, as this has progressed through, and now hits all three points, as this system suggests how your clothing should correctly fit, I’m safe to add this to my collection.

What If You’re Unable to get a Good Fit?

If nothing you try on seems to fit, you have a couple of options:

1. Buy a ‘larger’ size that fits your largest area (such as your shoulders), and visit a tailor, who will likely be able to advise you on how best to dress for your body type, and bring in the garment accordingly. I’ve actually written a fantastic complete guide on tailoring costs (taken from 30+ tailors), which you can access here, so you can get an idea of how costly this approach could be. I’d also advise to read an extended write up of this point in my companion article on actually finding clothes that fit, as it includes some more in depth caveats.
2. Look into custom clothing retailors, either online, or in person.

Other Considerations on How Clothes Should Fit

In every circumstance, I feel it’s also really important to understand why your fit may be wrong in the first place, so you don’t fall astray again.

Why Your Fit Was Wrong

Without going too in depth, you were likely ‘happy’ with your fit that you stumbled on to due to societal, psychological, and practical factors.

Firstly, our fit is usually influenced by the fashion in current society – for example, most people in the 80s were rocking the ultra-relaxed fit, despite that maybe not being the ‘best’ fit for them.

But this was expected, because psychologically, we are prone to follow the fashion of the time, and practically, those were the clothes in most plentiful circulation, so you were likely to end up buying it anyway.

However, it was likely that, if you were consciously trying to get a different fit – like you might be now – you could have probably found specialist stores for you.

Why Your Fit Continued To be Wrong

At some point, you may have started wearing clothes that didn’t ‘fit’ you best. And, given you’re looking this up now, it’s likely taken a while for you to realise that you might prefer something else.

This is because we get used to what we wear, and become ‘happy’ with what we’re currently wearing, even if there are aspects that don’t work for us.

The only way to really break out of this cycle is to make a conscious effort to improve it, like you’re likely doing now.

The Bottom Line…

So now you know how clothes should fit a man through the 3 point system, which you can use to assess if your clothes, or clothes you’re looking to pick up, fit.

If you consistently refer back to it, and build up some experience, I really believe you’ll find it much easier and less frustrating to find clothes that fit, and you’ll look better as a result.

But despite your new found general knowledge that will guide you no matter what, you may still be wondering how to find clothes that fit in a sea of brands that all fit differently – there’s so many other factors out there to consider with sizing, and problems people fall into, when they get into the real world.

Luckily, I’ve put together a cracking post on a bunch of points that will help you increase your experience, and get closer to having a perfect fit.