So what have I learned so far?

There's a fine line to be trodden between being a poseur and being subtly stylish.  Early on I realised that sticking with classics is a good approach.  For example, a man cannot go wrong with a pair of brogues.  This is an image that I liked -

I took this shot below of my own brogues last year, early on in my search for something to replace the anonymous shoes I was wearing.  A classic design, brogues work well with formal or casual wear and, for the man of mature years, are preferable to a pair of battered trainers (I'm at the age where I feel that trainers should be used exclusively for the purpose they were designed - sport!)