Exactly. At my age, I should be able to buy all my clothes in the High Street - but sadly that is not the case. Down the pub today almost everyone was badly dressed. People think you are 'stylish' if you are are wearing a jacket that buttons up rather than a fleece or zipper jacket. That is the way of the world. You either try harder or go with the flow.
Interesting what you say about the people in the pub,I think that there seems to be 3 main categories,
1, People who just don't care what they look like, ( scruffy fcuckers ).
2,People who dress practically with no thought for style, ie wearing a fleece on a cold day,or trainers because they are comfy.
3,More discerning people who take an interest in style and their appearance ( I suppose there is a sub group here of people who care but just get it wrong ).
I have sometimes tried to analyse why the way that I dress is important to me,the only reason I can think of is some kind of self satisfaction,I know that I am not too worried about what other people think of my dress sense ( apart from the GF,I know that she appreciates me dressing smartly ).
When you say about trying harder,I think that finding good quality smart looking clobber is becoming much harder year on year ( not one for going with the flow though,that would be dumbing down IMO ).