thoughts on “looking cool”

Posted in opinion
Trying To Be Stylish
We throw the word “cool” around a lot these days. I use it several times a day to describe a million different things, from my friend’s upcoming job interview, to the new album from Duke Hugh, to my mum saying she’s finished her laundry. One of my more troubling uses, though, is when I say someone “looks cool”. I’m not sure what the criterion is for this category… How does anyone judge who looks cool and who doesn’t?

One person’s look to me may be cool, but to my lovely aspiring banker friend Karoline may not be cool at all. We’re both different, so it’s no surprise. Four years into the friendship, we now move in different circles. Our “cool” barometers aren’t exactly the same as when we first met. And that’s okay.

But the circle I move in now is filled – mostly – with similar, like-minded people. We like a lot of the same things. We have a lot of the same ideals. We have similar tastes that stretch to our looks too, unsurprisingly. And this circle isn’t just friends and uni acquaintances anymore. It’s a professional circle that I’m slowly being surrounded by. These like-minded people aren’t just friends, they’re professionals now too.

Working World “Cool”

The industries I’m surrounded by are mostly creative – art, music, literature. I’m an English Literature graduate, an aspiring writer. Most of my university friends were from the Arts & Humanities department and with that definitely came a certain “look” – a lot of them have now moved into creative industry jobs.

I love these industries and everything they represent. They’ve always been the sort of jobs I knew I’d gravitate towards. But over the years, I’ve become more acutely aware of the pressures of “looking cool” and how that pressure has intensified now I’m transitioning into the professional world. A lot of the working women around me “look cool” and I’m conscious of how inferior I feel sometimes in comparison.

I’m not entirely sure how I judge this “cool” standard. But I know that the majority of the women I surround myself with seem to have a similar “cool” standard when it comes to looks. We all seem to agree when a certain person “looks cool” on this or that occasion. We all seem to like similar items of clothing and similar styles and similar wardrobe looking coolIf I had to describe it – and I can’t include everything or speak for everyone – I would sum it up this way: eclectic, colourful, mix & match, unique pieces, noteworthy accessories, vintage look, quirky, statement pieces… I’m not explaining it properly and encompassing everything and yet we all seem to agree when “so-and-so looks fly tonight”. I could probably point you to a few Pinterest boards that sum it up better with pictures than I can with my words (maybe a bit like this one or this one).

My “Cool” Problem

Here’s my problem though, and it’s intricate:

* I don’t have a natural eye for “cool” outfits, for putting this and that together and it looks amazing, for seeing a piece at a charity shop and knowing it will be a staple piece in my wardrobe, for quickly throwing things together and making it work effortlessly. My idea of a great outfit is leggings and my mum’s 80s Snoopy sweater. Done.


my favourite outfit, Snoopy sweater and leggings

* My time is so precious to me, to the point that I spend so much time in my day worrying about how little time I have in the day. Ridiculous. If I had extra hours in the day, I would probably spend the hour and a half it takes me on the rare occasions I decide to really try, and try and”look cool” (clothes, hair, makeup, nails, and all). But until it takes me fifteen minutes to do all that, I will generally reach for the easiest outfit I can.


* I don’t have the money right now to start creating a super diverse wardrobe. After culling 358694 things in September that I’d accumulated since I was twelve and that I never wore and would never wear again, my wardrobe shrank considerably. It’s only got the things I wear all the time and really love. But most of them aren’t the pieces that create that “cool look”, and I just don’t have the money right now to buy new pieces.


Basically, I’m too broke, and in terms of time, I just prioritise other things. And it’s frustrating that in light of this, and in light of the pressures and expectations on women to “look cool” in the workplace, especially in the industries I’ll probably gravitate towards, I won’t match up to other women who do “look cool”. It’s frustrating that there will be people who will pass judgments on me and my peers based on our ability to “look cool”, even if only subconsciously. It’s frustrating that I feel this pressure. Why should it matter? My look is no indication of how nice I am, or how interesting I am, or how well I can do my job.


My “Cool” Solution


I had a big (drunken) debate about “looking cool” with Harry a few weeks ago, and that’s what started all this. It made me think so hard about style and coolness, and I even gave “looking cool” a hardcore go one day. The details of our conversation are fuzzy, but essentially all my latent frustrations about never having “looked cool” and feeling overwhelmed by the pressures from this surfaced. I realised how prevalently the pressures to look a certain way still exist.


I thought I’d left them behind at school but if anything these pressure are even more stressful as an adult. My professional look is used as a judgment standard. I don’t begrudge anyone who looks absolutely steazy all the time – I admire them. But I don’t want anyone to judge me just because I don’t care enough to measure up in the same way.


I’ve realised there’s only one way to fix this for now. First step: stop saying someone “looks cool”. It’s a hugely ineffective, problematic generalisation about someone’s outfit. I’ve been trying to say “I really like this piece” or “I really like that combination”. Because then I’m commenting on someone’s look through my eyes only, and not frustratingly adding to the “cool” standard that people (read: me) subconsciously feel they should conform to.


The second part is only a semi-permanent fix and hopefully one day it won’t matter how I’m dressed. But until then… I spent a few hours one weekend trying to create and practice some outfits from my wardrobe. I tried to work out what my favourite pieces are and how I can wear them differently. I wrote down a list (typical me) of the “look” things I love (e.g.: rings, wearing lots of black, my Caterpillar boots, my Adidas trainers, anything that keeps me warm in winter…), and the ones I feel I should love but actually just don’t like personally (e.g.: creepers, chokers, any shoes with the slightest heel…).


I finished with some go-to looks that I’m happy with, that I can easily throw on so I won’t feel I’m sacrificing any time, but that will also make me feel like I measure up to the other “cool” women around me. I felt a little more comfortable afterwards, a little more calm. I got rid of everything I have for the sake of “looking cool” but that I don’t actually enjoy wearing.

And I think doing this exercise, I finally realised the most important thing about what “style” means to me. It just means wearing things I’m comfortable in and that contribute to making me feel good and calm and happy in my body. It’s about me, no one else. It’s not about what the other women are wearing, or what my friends are wearing, or what women in TV and films and magazines are wearing. It’s just about me.


Hopefully, one day, I won’t think about how “cool” I look at all and neither will anyone else.
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