The Sartorialist is great:
...but I think this demonstrates my main problem about fashion: only the good looking can do this.
Not a single fat person in these pictures. I'm not saying that they must out of some sense of equality or some kind of obligation. Clothes are not made for fat people probably because they just don't look good in anything. I should just lose weight if I want to look fashionable.
I speak from personal experience. I'm quite overweight -- like most americans -- and nothing I wore had any affect on how well I looked. So i just gave up on fashion years ago.
Nonsense. Tall guys look great in suits. I'm 5'7" and I always feel a bit like Tatoo from Fantasy Island (The Plane! The Plane!) when I put on a suit.
Hint: many clothes come in [S]hort, [R]egular, and [T]all length variations. It's good to figure out which one you are and buy the appropriately proportioned one, or err on the side of too long and have a tailor crop it for you.
Compare this young guy: http://www.thesartorialist.com/photos/12010TanLeather3822Web...
with this older man: http://www.thesartorialist.com/photos/11810DGscarf3456Web.jp...
The second man has serious style, and his outfit could be tailored to a heavier man. However, if you're not a young, handsome guy who pays so much attention to your hairstyle that people will notice it before your epic static cling, you can't get away with the first man's look.
It doesn't go together, it doesn't fit, it doesn't look expensive and showy, it's not crowing designer labels, it's not bold and contrasty and awesome, the only redeeming feature it has is that he's obviously put effort into making himself look so unusual. And that's fine, he wins points simply for doing that instead of wearing jeans and a t-shirt.
But he doesn't look fashionable. Does he?
I don't know if I'm really crazy enough to recommend that you try dressing like Henry VIII or Benjamin Franklin; but keep in mind that it's hypothetically possible, at least.
(Then again, how much _could_ anyone do to you if you went out to dinner or got on a subway dressed in the best fashions of 250 years ago (other than the Scots Highland style of dress which requires a dagger tucked into the left stocking)? I could see certain sorts of people recommending it as a character- or determination-building exercise...)
More seriously, though, I agree with the idea that Winston Churchill -- or G.K. Chesterton, legendarily overweight but positively dapper -- might be a good starting point.
A bigger concern is that most sporrans are made out of sealskin, which is effectively impossible to take into the US. The one time I looked at taking my kilt with me to the US I decided it would be much easier to buy an all-leather sporran, even though they don't look as nice.
Here, at least, a full dress kilt is acceptable as 'black tie' in place of a tux.
For example, there's a young CS student at my school who wears a long brown leather coat and a pirate-ish hat. The two problems are: Who over the age of 8 dresses up like a pirate? and he's bald-faced, sneaker-wearing, and has a t-shirt under the coat.