Personally I'm in my late 40's and wear dark clothes. Usually black trousers or jeans with a shirt and jumper in cold weather. I'm always smart casual. Never wear anything ripped unless I've had some sort of accident! Nothing too showy, I'd rather not stand out apart from one thing, I always wear my black fedora hat when out. In the summer it is great from keeping the sun out of my eyes and in the winter it keeps my head dry and warm. I have a full head of hair so it isn't worn for vanity but really because I can put my head down and march forward quickly and usually people get out of the way. Handy as I live in the centre of a city.
The hat does sometimes attract unwanted attention, usually from drunk up vagrants or general morons who generally shout "Like the hat mate".