My 2 cents is to stay away from desert boots, they are so played out right now. they're even in the mid range department stores in Australia now..
go for a different classic instead like japanese market redwings or something. I basically actually agree with HW and others tho, the key is a couple of really good pairs of shoes and a good watch, the rest should be basic and plain staples. the watch and shoes should be classic and basic as well.
Individuality…completely prescribed by Hello World…
If everyone else in your social group is wearing head to foot superdry, topman or other UK wide highstreet, wearing an oxford shirt is a big expression of indivudal dressing. The person who asked for help was just an ordinary guy (not an insult), not someone who has spent 10 years reading about fashion trends and the latest hype brands. Redwings means nothing to them so the expense is not justified.
Otherwise I wuld have just said get a few grand and go to the basement of DSM.
Hence the advice was for how to just smarten up and have that standard well dressed late 30's look which I gave an example of an was agreed upon.
The stlyes on here are all extremely narrow focused with brands and expenditure that people with other commitments cannot justify and would not necessary have the confidence to wear in their social group due to differences in style.
Milspex I do think you dress very well and obviously spend a considerable ammount of time thinking about and sourcing items, but you have to considered that you have to adapt and own clothing that is suitable for all social occasions. Hence you ahve your main casual look, then you step up to a "clapton" for smart casual or casual office work, a blazer or a jacket or something for fancy resturants or other requirements, A suit is required for most people for work as well.
Not many people get to wear exactly what they want every day for all ocassions, so socially appropriate attire is always required.
Generally your wife or girlfriend will have some input into forcing these issues if you turn up to a dinner party dressed like a vietnam vet when it was more smart casual affair.