Self Esteem: My Greatest Style Influence

Where does one’s interest in style come from and what are the influences?  A complex set of interrelated experiences, no doubt, and difficult to identify.  In my case, I have 4 siblings, each stylish in their own individual ways.

Both my older sisters have long been fashionistas and one of them designed her own clothes for quite some time. She had a friend who was an extremely talented seamstress; she would sketch a design idea on a piece of paper and her seamstress could translate that into a bespoke piece of clothing within 48 hours.  I remember my sister discussing design ideas with me as a teen; not because she wanted my opinions but I suspect because I was one of the few who would listen as she spewed style ideas.  So I guess I am in touch with my feminine side; older sisters do that for you.

But there were many male influences also. My younger brother, for example, can pull off a really cool style, a sort of ‘gangster chic’ that I would not have the confidence to attempt. My older brother in his younger days was a serious fashionista as well, though he has a much more reserved approach now he approaches 50. This was a man whose wardrobe included leather trousers and at one time he sported a curly perm! Then again, it was the 80s and this was pretty cool at the time, though cringe-worthy now. One of the great things about turning 16 or 17 is that I was finally able to borrow big brother’s clothes (almost invariably without permission). I might also think of one of my sisters’ boyfriends who had more shoes than she did!  Before meeting him I had no idea that men’s shoes could come in such a wide variety of colours, shapes and styles.

I also happened to have a number of stylish men among my friends. I am fortunate to have remained friends with a bunch of guys from my secondary school days, even though we live in scattered places across the world.  Many of them are stylish men.  Some unfortunately are less so…  One of my oldest friends is perhaps one of the most consistently well dressed men I know.  As teenagers he and I had an unofficial style competition going on; then again maybe that was just me competing with him and not the other way round….  Whenever we went out we usually stopped off at his house last and when he came out I’d have a mental check to see which of us was the better dressed.  I can only recall one instance in which I think I won….

I’ve also worked with a number of stylish men over the years in a variety of industry contexts. One older colleague who is certainly the best-dressed man over 60 that I know is always immaculate. I’ve told him that when I grow up I want to be like him! 🙂 All of these encounters, of course, influence one’s approach to and interest in style.

My guess, however, is that my greatest style influence has not been any of these experiences, as helpful and as formative as they have been.  I am pretty convinced that my greatest style influence is in fact rooted in struggles with poor self-esteem and my discovery of style as a mechanism by which I could navigate periodic assaults of self-doubt.

Our female counterparts figured this out ages ago.  Dressing stylishly can make you feel better about yourself and about the way you view the world. Crucially, style can also influence the way people respond to you.  I figured this out when I was 17.

I had been wrestling with poor self-esteem since the onset of adolescence and was painfully shy outside of my immediate friendship circle. Moving at age 16 to a mixed A’Level college from an all-boys grammar school was like arriving on the doorsteps of heaven. Unfortunately, whilst I was very interested in girls, few of them were interested in me.  Actually, I have no idea whether they were interested or not, because very few of them appeared to be aware that I existed.  But quite by accident I discovered the power of style.

I had agreed to be in a school play.  Me!  Afraid to speak in public, me! The part even had a small dance routine!!  Me!! To this day I still cannot work out how I was persuaded to do this. I must have temporarily taken leave of my senses. I was to play the part of a wealthy man being taken advantage of by his girlfriend. Don’t remember anything else of the plot line… To play the part I needed to be well dressed but this was a student production without wardrobe, props, anything.  So I raided my own wardrobe put together an ensemble and came to the dress rehearsal.  I was terrified and wondered how the heck I had got myself into this.

Two things happened.  First, I discovered that I could ‘hide’ behind the outfit.  People apparently didn’t see the kid nearly paralysed with stage fright. They saw the well-dressed character of the play.  Incredible.  Second, I discovered that those girls whose attention I had been trying to get all year, suddenly discovered I existed now that I was not dressed in my usual college uniform.  Weird stuff this….  I was still the shy geeky kid, who didn’t know quite know how to talk to girls, or indeed to anyone if it involved speaking in public.  But with a change of clothing people reacted to me differently.  Most unexpectedly of all, I actually felt different.  I felt a little better about myself. It’s a bit like the Clark Kent/Superman transformation; same guy but a change of outfit can bring a change of attitude.

Ever since then I’ve been very interested in style, especially when I feel insecure or inadequate and need a confidence boost.  So if I’ve got a big meeting or complex situation I think carefully about what I’m going to wear. Indeed, if I look back on my life over the last decade or so, whenever there has been a really big issue on the horizon or new job that I don’t feel quite up to, or a complex situation that I feel is beyond me I have often taken refuge in clothing appropriate to that context. I figure if you don’t know quite what you are doing, if you at least look like you do, or look the part, or look like you belong you might just be able to hide behind the outfit. And people may not see the kid nearly paralysed by stage fright; they might instead see the character that you are playing. Most importantly, you might just find that you feel differently, just a wee bit less lacking in confidence when you are appropriately attired.

But I can’t pretend that my interest in style is only a functional one. I’d be lying if I didn’t also say that I’m interested in style cause I quite like it.  The fact that a sense of style also has benefits for one’s self esteem is icing on the cake.

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