On more than one occasion in the past, I have been accused of being pretentious in the way I dress. Presumably, that means those people think I was pretending to be something I was not.

Sometimes, whether accused of it or not, that may be true. After all, it is a fear of appearing pretentious or out of place that makes one feel self-conscious about wearing particular items. It is the reason I don’t wear a trilby, braces or a cravat.

I’d love to, but I don’t think I could ‘pull them off’. In other words, I would be afraid I was pretending (so being pretentious).

But how do you stop pretending and become the person that can wear those more extravagant clothes? I think the important link here is to another group of words: affected, conceited, self-conscious. Style should be casual, easy and unforced.

It is linked to the Italian concept of sprezzatura. It was captured by Hardy Amies’s edict to forget all about your well-chosen clothes as soon as you step out the door. The tendency not to do it was expressed by Coco Chanel’s recommendation to look in the mirror before you leave the house, and take one item off.

If clothes are affected, it means they are false and do not suit the personality that wears them. That person could be conceited, and will probably be self-conscious, because they do not suit him and his character.

But we’re left with another phrase to define: that which suits someone’s character. I suggest this breaks down into three areas:

Comfort and habit
Men that are at ease in their clothes have dressed that way for a long time.

Yesterday I was wearing a pair of bright white trousers that, having never worn anything similar before, made me a little self-conscious. Then I saw a man coming the other way, wearing similarly blazing-white trousers, a double-breasted blazer, co-respondent shoes and a cravat. On its face, his outfit was more pretentious than mine. But he had obviously worn similar clothes for years and felt entirely at home in them. He was not pretending to be anything.

So youth and a changing wardrobe are a disadvantage. But this does not mean you should not wear anything daring. It means you should take it one step at a time.

I’ve only been wearing pocket handkerchiefs in my jackets for around two years. At some point in the next 10 years I will probably start wearing formal hats – it will feel odd the first time, but not as odd as if I started today. I rarely wear both a tie and a handkerchief, but recently I have decided I like to wear a white linen square on more formal occasions – when I am on stage at a conference or ceremony, for example.

Being ill at ease and self-conscious in your clothing often results in adjusting it constantly – tugging at the pocket handkerchief, adjusting the tie and glancing in every reflective surface. Equally, this discomfort can be caused by clothes that are just too tight, or restrict you.

To avoid pretension you must be comfortable in your clothes. This is a result of both mental and physical comfort.

Knowledge and rule-breaking
Knowing the history of the clothes you are wearing, what they were originally intended for and what rules were formed as a result is a big plus.

A man that wears a strongly pinstriped jacket with pale jeans would usually be viewed as crass and ignorant. Possibly pretentious.

But if that man is Alan Flusser, and you know that he knows every rule and guideline there is, you pause and reconsider. He is breaking those rules on purpose and with an aim in mind. You may think he fails, but you can’t argue that he is necessarily wrong.

Equally, wearing unusual clothes with the propriety they were intended for stops you pretending to be anything you are not. Knowing and applying the rules well stops you looking affected. It should also help with the first point – making you more at ease.

Freedom of expression
As with the Flusser example, your dress will not appear affected or false if you constantly adapt rules to your own taste. If you mimic another man exactly you are being false; you are trying to affect him. If you mimic a man or group from the past, you are being false, for those men are not you.

Take the knowledge that enables you to tick the second point on this list, and then twist it to your own personality. You then cannot be false because you are you. And you’re much more likely to feel comfortable and not check your reflection in car windows.

Obsessively following rules just makes you a nerd and a bore.

These are my instinctive ideas on what stops a man being pretentious, and allows him to deny that accusation. I think you need all three to qualify. And I am not suggesting by any means that I have always qualified. Any man with any interest in clothes has memories of ill-considered clothing that make him cringe today.

But we live and learn, and without experimentation we would never learn what inspires us, what we want to mimic and what we want to twist to our own personality.