Gee, I am impressed that you are putting so much thought into it.
I agree with you, it is *so* hard to know where to start and I struggle with it continuously on a weekly basis. I find it even harder to look stylish and pulled together in the summer when I feel so hot and sticky and my main priority is to be cool and comfortable. (I'm in QLD, so a big wave from one Aussie to another! :-))
The biggest thing I learnt when I started out is that how I thought I looked in the mirror was not how I looked on film (and I assume to others). I got quite obsessive for a while, taking photos of my outfit every morning to check and see whether my outfit looked balanced. These days I don't tend to bother, unless it is for a special occasion, or I am concerned about whether a look "works" or not. (Such as right now - I seriously don't care how I look - I am sitting here in my sweaty and smelly exercise gear, and I must confess I'm not particularly bothered about doing anything other than having a shower and putting on my pj's!)
I've also learnt that sometimes the thing that takes an outfit from OK, to great is actually the attention to detail - such as the choice of shoes, jewellery, belt, handbags etc, rather than each particular item of clothing. That was a real eye-opener for me. So, for instance, if you have a lot of grey and black, you might consider a bright red necklace to "lift" the outfit. Or if the outfit is mostly grey, you might consider teeming it with yellow and white. (This is one of my favourite colour combos!)
I promise you that yes, a small detail such as this really can make a very big difference. The best thing is that it can be cheap and it is practical, no matter what your life-stage or the time of year. It has now become second nature that when I put on an outfit to just pay a moment to consider the accessory/ies I think will complete the look. You can do this even when it is really hot.
As I know the members here are so very supportive, I propose you consider having a little "play" with your clothes and accessories and come up with a couple of outfit combos. Then be brave and submit a request for feedback and suggestions. I have seen other members do this in the past (and I have done this myself) and have found it so very useful and helpful to receive the insights and advice from other members.
Have a fun and creative weekend exploring!