Confidence and Dressing Well

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When a man doesn’t know me very well but knows, perhaps a little too well, what I write about, he often seeks to bond with me by chorusing my views on the general decline of menswear. “Most people” they begin “haven’t got a clue how to dress anymore, have they? It’s all too-long trousers worn like jeans, isn’t it? Clip-on bow ties and rented morning dress…”

Much to their surprise, I do not rejoice in this sorry state of affairs. Being a man who, for the most part, wishes that he lived in a bygone age in order not to stand out for being so interested in outward appearance, I despair with a heavy heart. Aestheticism is now an underground world; a secret, smoky society of like-minded individuals who know the value of dressing well and have, for the most part, given up in recruiting new members to the club.

Who can blame them? Most of the well-dressed chaps I know receive more mockery than praise and it is hardly surprising that they would seek out those who offer sympathetic company and an easy ear. The world is a dark and decaying place full of branded sweatshirts and luminous trainers; the company of a fellow aesthete, in agreeable surroundings, offers escape and a chance to reinforce self-esteem. The key to stoic defiance in maintaining good attire is lashings of self-confidence.

Self-confidence in such matters is not easy to come by. Though many women assume men have been afforded an unsporting advantage when it comes to confidence, dressing with self-assuredness is an area in which women consistently outshine men.

I was recently introduced to the husband of a work colleague who recounted to me his lifelong worries of the wardrobe. One girlfriend had been so viciously critical of his attire that she had, quite without his knowledge, begun to pile all the items that she didn’t like into a bin bag which she was due to throw out. When he discovered her in the act, she merely repeated her claim that he wore terrible clothing and that he didn’t know what he was doing when it came to sartorial matters.

Had such an unfortunate event befallen me, quite another bag would have been duly stuffed and sent on its way. I would have defended my taste and style to the hilt. As it was, and indeed is with so many men, the confidence required for this defence cannot be summoned. Believing themselves to be outflanked, they simply comply, keep calm and carry on.

Style is personal, but it starts with research. This research builds into knowledge and with knowledge, a man can arm himself when entering the fray of what is, to women, a paradise but, to many men, a battlefield; the world of clothing retail. Knowledge, properly applied, builds confidence and confidence is the key to developing, with or without the assistance of others, a personal aesthetic that is unassailable. For even when they cry that you have it wrong, you are well equipped to issue the rebuttal.


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Winston Chesterfield is an amateur composer, fashion blogger, trained lawyer and style aficionado. He lives in Westminster, London and blogs at www.levraiwinston.com.

Comments

  1. AFJ says:

    A car starts.

    A research begins.

  2. Adam Ford says:

    I take my lead from Steve McQueen & Don Draper. Ladies (most) still love a well dressed, stylish chap. That’s what counts..not the SuperDry guys.

  3. JerryS says:

    Great article!
    Women give me compliments on my dress almost daily. Sneers come from other males, however those doing the sneering are usually dressed worse than a homeless beggar in 19th century Calcutta.

  4. Will says:

    As ever; all good points Winston.
    Though, of course, there were always badly dressed men whichever decade you look back to. Plenty has been said, not least on these pages, about the current addiction many men have for the ‘football kit uniform’ worn as their constant casual wardrobe but it is still a shame.
    Some role models, like Carey Grant, Bond and McQueen (as Adam suggests above) are hugely valuable in judging what ideas can work for ones own style, but as you say reading up on the topic (and creating further free content for others to read) can only be a good thing.

  5. dave says:

    A tailor or super expensive clothes will never make up for a gym body.
    You could put a pair of Levis and gap t shirt on a man- even in his mid 50s if he takes care of himself and he would look good.

    Most people don’t have the time and when they learn, it costs them a fortune.
    Ignorance is bliss. I am just learning that. everything I like, booze, coffee, food, clothes, car, stuff, etc had to be very good or the best. This is why I don’t try things that are the best anymore- its value is fleeting, illiquid, and depreciating.

    Since 08 I can not for material anything, and prefer liquidity to overdrawn accounts, constantly searching for the best competing with my imaginary millions of fashion competitors.

    It just doesn’t matter anymore.

  6. Fonda says:

    Style and enjoying ones own wardrobe is priceless. Confidence comes with time but that in itself should not prevent one from exploring. Now more than ever a man dressing for himself is vital…there are far too many out there lost in the wilderness of standard ‘fashion wear’ and compliance with norms. I love my three piece suits and accessories that go with them, and my wife and daughters enjoy and appreciate the site of a well dressed and confident man.

    Being creative and dressing well is fun and adds to my day…why would I give that up?

  7. Jake says:

    “A tailor or super expensive clothes will never make up for a gym body.
    You could put a pair of Levis and gap t shirt on a man- even in his mid 50s if he takes care of himself and he would look good. ”

    True enough but that goes both ways. Those (and it’s most of the male population, to be fair) who don’t have a gym body, or are a little out of shape, could work wonders by carefully-chosen properly-fitting clothes, rather than accentuating their shortcomings by dressing like a slob.

    By the same token, if you *are* lucky enough to have the physique of a Greek God, then you will look absolutely fantastic in good clothes, so surely it is a shame to look merely good in average clothes?

  8. dave says:

    T-shirt, jeans a personal trainer- healthy body, healthy attitude and liquidity trump pale office shulb or dandy everytime- is about getting women, period- not to make other men jealous, thats a side benefit- especially when you are pushing 40 and look better than the interns or young guys.

  9. john broewn says:

    after reading all of the review i could not allow mines to go without stating one . a man clothes do make him he makes the clothes . one gentleman stated something about a tshirt and jean, and it is true all men can not pull that off without a very nice body, but if this man has style he most truly can with it ever being question , because he makes the clothes. true nice clothes are very expensive, but if one shops at ones local thrift store you find some of the most beautiful clothing, and at the cost from other who paid the true price of what they cost. so with that said the beauty for a man to look nice is really for the ladies and i do love the ladies and i being doing the damn thing since i was a little man. peace