Sure, no problem. Look all I’ve been trying to convey is that although there are some basic rules of fashion, there is no clear defining line as to what looks good and what doesn’t. Sure, as with anything else, the more you know about a particular topic the better the odds that you’ll get thing “right” – wrong, in this case being a fashion faux pas. And yes, there are glaring examples of bad taste; I am particularly miffed by the longevity of the patent leather white shoes and belt combo favored by many a wealthy retiree in Southern Fla. Glad that all the years I spent working in the fashion world were in the NYC/CT area for had it been in Florida, chances are high I would have gone Postal at some point.
Anyhow, as for the case that occupies us here, Obama’s style, I happen to disagree with your assessment of what he should/n’t wear for I find your generalizations both too broad and confining. As I wrote in my prior post, skin tone was only one of any number of qualifiers I used when directing my clients to any particular style. And no, I certainly don’t think that black men in general either “look threatening or like waiters” in any particular suit. Odds are though, that with the amount of inventory we carried, I could make just about anyone look like one of those two. However, to my knowledge, none of my costumers were part of the Cosa Nostra nor did they wait tables at Portofino*, thus that was never a look I went for.
Obama, visually, appears to me as the kind of costumer that made my life easy, for he has both the body-type and flesh tone that would allow me to get him into many/most of our suits and styles – from a very traditional Burberry’s to a happening, stylized, three-button Donna Karan (loved her fabrics). Colors? Well, again, I don’t go by hard and fast rules, but rather intuition and practicality. The former gives me a mental image of the finished product or rather where I want to go with the client, the latter meaning that it’s rather hard to get people out of their comfort zones, thus instead of wasting time trying to convince to try something new/different, you do the best you can within the parameters given. Patterns and hues that work on a particular skin-tone I rather asses in person and not through pictures, TV images or style guides.
Best clients to work with? Without a doubt, the guys (or the wives) that came in and said “I/we like your look. Could you show me something in that style?” I mean, what’s not to love? Walking advertisements for my (former) craft they became. 
In any event, apologies for the ill-timed invective in my last post; it just happens that I can be a bit of a smug prick myself. Tell you what though, I can now see us getting together and not having a go at our respective bald pates – how’s that song go? Something to talk about…
About time too.
PS-For the shiny pate I recommend any number of men’s anti-shine scrubs. Nivea’s products are always a good bet.
*City Island, Bronx. Great restaurant.