The Question Of Trying


One of the most fascinating accusations levelled at me is that, in my manner of dress, I try far too hard. This has always been a sore point for me but not, as you might expect, because I experience personal wounding from the insult. Rather it is frustratingly perplexing to me that commentators can deliver in the manner of a fait accompli such dissatisfaction with, not a result, but the appearance of effort in attaining that result. Additionally, the pretence of such commentators with regards to their acquaintance with the intimacies of my mental and physical exertions when we do not even maintain the slightest sense of a communicative relationship is absolutely staggering. An aesthetic criticism seems legitimate to me; “Too fussy”, “Too derivative”, “Too bright” – these are opinions based on evidence. “You’re trying WAY too hard” on the other hand is not based on evidence but is simply a speculation.

Firstly, the concept of trying is a relative one. People who are aesthetically inclined and colour-minded may naturally find it easier to throw a few items together and make an outfit. In much the same way that a skilled composer can produce an original and beautiful tune in a matter of minutes, or an artist produce a compelling portrait in under an hour; the result is not always a sign of considerable time-investment. Secondly, it should not be that a sign of trying, phantom or otherwise, is so repugnant to the man in the street. Effort is denigrated too often and too wantonly and has become a dirty word in an increasingly laid-back, barely sentient, dozy excuse for a developed world. Trying is apparently wrong and trying too hard a mortal sin.

My participation in a recent Esquire competition to find Britain’s Best Dressed Real Man exposed me to the opinion of a vast array of forum-trawlers, many of whom exhibited sheer indignation and contempt for any entry that appeared to involve ‘trying.’ What was most interesting was that the most complimentary and the most critical rounded on the same issue; “…You can see what he is trying to do here” vs. “…he is trying waaaaaaay too hard.” Again, the appearance of trying (however disingenuous that effect might be) the subject of chief concern; not colour, not pattern, not the mixture of fabrics.

A friend informed me that any number of entries in the competition would receive such critiques because individuals do not consider themselves ‘qualified’ enough to analyse compositions for their result because they cannot compute the personal effort required on their behalf to simulate the same effect.

This is perhaps rather harsh, and as speculative a charge as that of someone telling me I try too hard, but it does touch upon a deeper sociological topic: ‘trying’, in relation to creativity, is the easiest thing to stigmatise as the results of an aesthetic pursuit are always subjective. It also attacks the integrity of the creator to mark a result as one of industry rather than inspiration. Unless such bitterness is expunged, I expect in ten years or so a gentleman wearing anything more involved than a GAP fleece and a pair of training shoes to be scorned as an, ahem, ‘trying’ individual.


  1. Bill Coven said:


    There’s a difference between making an effort to look nice every day and focusing 100% on looking absolutely absurd. No one looks at you and says, “that’s a well-dressed man.” They look at you and say, “he’s trying to make me look at him.”

    October 17, 2010
  2. John Hannen said:

    I also disagree with the article which displays the same lack of self-awareness which informs the man’s dress

    It’s possible to dress bodly, with style without overcomplicating your dress and looking like a chamaeleon on a tartan rug, sprinkled with confetti and lit up with strobes

    One should choose pieces which complement each other rather than fight each other for the attention of the onlooker

    this may seem like a harsh comment but when one invites criticism then this happens

    October 17, 2010
  3. Bill and John,

    I presume from your comments that you are referring to me personally?

    Best regards,


    October 17, 2010
  4. John Hannen said:

    Who else would I be referring to?

    You present yourself in a way that can only be percieved as an attempt to gain attention. You then write an article that makes assumptions on the behalf of critics that don’t really address the criticisms but only seek to justify your actions and this is made public in a way that can only generate heat and garner you more attention and then you ask when any comments it provokes are aimed at you? Sir you are trolling, both on the internets and in public.
    I bid you good day.

    October 18, 2010
  5. The Classicist said:

    Dear Winston– I am one of those who accused you ” trying too hard.” (Dinner jacket, jeans, opera pumps.) Basically it was my shorthand for saying it didn’t work, (in my opinion.) “Trying too hard” may mean that too much thought went into creating dissonance for the sake of dissonance, shock value, or that the results were too transparently contrived for the end results.
    As to previous comments: Does it matter if you seek attention, (or not?)
    What I see is someone who loves beautiful clothes, fabrics, patterns, colours, and has the taste and imagination AS AN ARTIST, to put them together. (Maybe great painters, writers, composers, are/were merely seeking attention.)
    –The Classicist

    October 18, 2010
  6. I’ll ignore most of the diatribe.

    The main points are that there is a lot of pot/kettle talk about trolling here, a visual exaggeration of an aesthetic (chameleons and tartan rugs) and general hypocrisy; “You then write an article that makes assumptions on the behalf of critics” vs. the fact that those critics presume to know the inner workings of my mind and are somehow mysteriously present to witness the ‘effort’ in my dress.

    Bill clearly believes he speaks for everybody; “No one looks at you and says, “that’s a well-dressed man.” They look at you and say, “he’s trying to make me look at him.””

    Finally, I did address the criticisms – as far as I could with the tiny amount of information supplied in the comments. What did you expect? “Ok, some people have been saying I try too hard…and maybe I do”?

    Why do you even read my column if you do not like my aesthetic?

    Why do you even waste time on me if I am simply a troll?

    The real provocation I had hoped for would be what The Classicist has provided; information as to what the ‘shorthand’ stands for: “…may mean that too much thought went into creating dissonance for the sake of dissonance, shock value, or that the results were too transparently contrived for the end results.”

    This is far more interesting, and valuable to others, than a personal and rather boring attack on my taste.

    October 18, 2010
  7. Ikarus said:

    There’s this idea of very ascetic approach to dressing circling around web promoted by those taking themselves too seriously for their own good. Ironically they’re the one’s that are trying the hardest.

    October 18, 2010
  8. Canadian said:

    A man’s clothes should draw attention to the man, not to the clothes themselves.

    October 18, 2010
  9. keithc2608 said:

    Keep on ‘trying to hard’ too many people don’t. I went out drinking in my small town on saturday and people might think I tried too hard; I put on some brown brogues, dark jeans, white button down, grey cardigan and a red, orange and pink striped wool tie. Most people looked messy, or looked like they had put minimum effort in. By people, I mean men.
    So keep trying to hard; to the haters, keep on hating.

    October 18, 2010
  10. Will said:

    Not quite sure the comments were fair following this post. I agree that some people can look rather like an over-the-top Peacock’s when they perhaps should tone down parts of their outfit or indeed wardrobe. But this is personal preference.
    I agree with Winston that one should never use ‘trying too hard’ as a criticism, as this suggests making an effort should in some way be frowned upon.
    A touch of colour and style is never something to be ashamed of.

    October 18, 2010
  11. Jim said:

    Hmm. It depends on the intention of the dresser. At the end of the day overly elaborate and fussy dress is simply not manly. Clearly if the dresser prefers dandifaction that is not a problem for him so long as he can bear disapproving stares and snide remarks.

    Cary Grant would never be accused of “trying too hard” even though he undoubtedly did try very hard. He radiated a social ease and insouciance which is rather difficult to replicate when bedecked like a popinjay. That is the ideal: to dress well without seeming to try, even if everyone really knows that you have.

    Standards of dress have definitely relaxed and thus it takes less to be considered a dandy. This is a little lamentable but it is still possible to dress with dash without raising the wrong sort of attention.

    All the same, I would not be worried if accused by Joe Public of “trying too hard.” However, were visitors to an esoteric style forum to make the same accusation…

    October 18, 2010
  12. The Classicist said:

    It’s time to worry when you are accused of not trying hard enough!
    –The Classicist

    October 18, 2010
  13. Kyl said:

    It is interesting that attempting to appear effortless is the ideal– while showing no effort in your appearance is the reality for many. The funny thing about dressing well is that we do it to impress others, while saying to ourselves that, “I’m wearing this because I feel like it.” Anyone who wears clothes has to settle the conflict that can occur between these two points of view.

    October 18, 2010
  14. Neil S said:

    Mr Chesterfield has raised an important issue of style here – What is trying too hard? It is a question that depends upon the gentleman, his sartorial selections and the quality of his audience. To raise the question is meritorious; to attack Mr Chesterfield personally is unwarranted.

    For a gentleman to make the effort contrary to pressure from his friends demonstrates his superior standards and often, their marked lack of standards. As to the end result of “trying too hard” or not enough, that is, what is ghastly or sublime, that is another debate entirely.

    October 20, 2010
  15. Go get ’em Winston. We all have to “try” to a certain degree. As you once told me, “stick to your stripes”.
    Wonderfully done, Winston.

    Good day to you

    October 24, 2010
  16. Phil said:

    Dressing well is always relative to the context in which you are presenting yourself. Context is where you are going, who you are going to be with, why you are going there, etc. There are so many factors that determine what it means to dress well yet it should always come rather naturally, just like speech.

    1. to attempt to do or accomplish: Try it before you say it’s simple.

    2. to test the effect or result of (often fol. by out ): to try a new method; to try a recipe out.

    3. to endeavor to evaluate by experiment or experience: to try a new field; to try a new book.

    4. to test the quality, value, fitness, accuracy, etc., of

    If you understand the context for which you are dressing up, there should be very little room left for trying anything.

    October 30, 2010

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