Sometimes I wonder how many of the supposed classic clothing "rules" were for real, and how many are a faux-classic, modern affectation that has crept into the collective (sub)concious. Much the same as how many of the supposedly ancient Scottish tartans and so on were actually inventions of the Celtic revival period in the late 19th Century as opposed to the pre-Highland Clearance, genuine article. Bear in mind that in all probability most of us today are better off than folks would have been back in the 30s or 40s, with more disposable income and better wardrobes. My personal view tends towards the Baron's slant on things: experiement and see what works. Of course this can lead to some howlers, but that's how you learn (I still regret the day eight and a half years ago when I went out in matching brown shirt and trousers, and blue peacoat, just didn't work for me, and left me with a mortal fear of mixing blue and brown. That said, the number of folks on here who do it well has convinced me it's not something to rule out ad infinitum). Naturally we don't all have anywhere near as\extensive a suit collection as the good Baron (very impressive, Sir!), but nonetheless I think there's always room to experiment. Do it at home in the evening - see what looks good together. Take some tips from the photos of those on the FL who do it so well - the ladies have been doing this for generations, why shouldn't we men catch up?
Start with a few classic looks, say one really good suit, try different colour shirts and tie combinations, see what works with a pocket square, and shoes.... One rule that I do think is sound is matching the belt (brown or black) to the shoes. But in general, I'd think of "rules" as not so much hard and fast rules as advice.
As memory serves, the old rule was "Black for town, in country - brown." I don't know its origin or the thinking behind it, but I would suggest that it had something to do with the idea of black being more formal, brown being something relaxed. Bearing in mind that many of these so-called rules evolved out of the upper and upper-middle classes who would probably have been in the city through the week, then off to the country estate at the weekend to do a spot of game shooting or fishing. I'm figuring too that in the 30s it would have been de riguer for those worknig in the City of London to be turning up for work in a stroller...?
In London today, you certainly do see a lot of brown. The big trend of the past 12 months or so seems to have been very dark navy or black pinstripe suits with relatively conservative ties, light shirts (pink I've seen a lot of, as well as blues, ivories and so on), and light tan coloured shoes. The tan and navy combination I'm not convinced of for myself, but it's certainly around as a fashion thing. There don't seem to be so many 'rules' being followed, though it does seems to me that you see certain tribal characteristics - e.g. the lawyers I see around the courts tend to dress very classic, whereas City trader types you can pick out by their more modern cuts, bright shirts, wide splayed shirt collars and tie knots the size of a fist. lol
Certainly, though personally I would choose a deeper red such as maroon.
Thanks for the reply!
Gustin Vintage Heavyweight Sweatshirt - Natural Rainbow Nep - $119 Rugged 14oz cotton that gets better with every wear. 
Grant Stone Diesel Boot Dark Olive Chromexcel - #395 Goodyear welted, Horween Chromexcel, classic good looks. 
Himel Bros. - The Ross Mk. 1 Leather Jacket Classic D-pocket motorcycle/aviator style jacket. 
