As long as it's clean does it matter? Having said that I gag at Chav wear these days. I once tried on a pair of 3/4 length trousers and my Mrs. nearly died of laughter.
I generally wear what Mrs KH tells me to (I can't be bothered) but she does tend to pick me work shirts in pastels and I prefer a stronger colour or stripe.
Actually I'm pretty particular about what I wear at work and much as I love designer suits/shirts/shoes the fact is a) the cost is disproportionate to the benefit in most cases - unless you're James Bond or a very successful bond trader - and
designer suits/shirts/shoes just do not (unless designed to do so) travel well in a rucksack. Hackett or Lewin shirts are all very well, but I've got to iron the buggers and they never look as good as when they were first in the packet. It's also more difficult to mix shirt suppliers as they come in different sizes, shapes, etc. Shopping's for girls IMO unless it involves some serious hardware. I prefer classic lines and will spend for a loved acquisition which will last. My watch for example is a basic Longines with a leather strap which I have had for 15 years. And you can only wear one watch at a time.
Like RR I'm half bald so get used to it. No point in going to a fancy hairdresser. So I just give it a number 2. I think shaved heads only work if you have soft features. Shave my head and I would look like an Essex drug dealer.
Weekends; shorts with anything. Even in the depths of winter. In fact I'd wear nothing at all being something of a sensual minimalist but I'd probably be prosecuted.