As much as I would love to habitually wear Hawaiian shirts (and I did find a load of mine the other day), I think that would be a bit too much for work! The ‘tache would probably be a bit too much for the rest of society.
Work is corporate rather than startup, so has to be a bit more responsible. Mind you, no one seems to care what I wear here as long as the logos are not insulting/rude.
The main problem I have is one of size; I’m about 6′ 7″ with a 42/44″ chest and longish arms, so generic shirts never seem to be either long enough or have long enough arms. I can get by with the Charles Tyrwhitt ‘long’ shirts in their ‘fitted’ range most days, but none of the casual ones really set me alight. I’ll give some more places a look in this weekend and see what is what.
Shoes are another matter completely. I’d normally go for a pair of casual brogues, but have been told that something like a Chelsea boot would be better given a) my height and b) the way that a lot of trousers are a little too short for me. A shame I don’t like that style of shoe (he said wearing a pair of Reebok Nanos…)