...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.
Churchill was overweight and he wasn't too bad of a dresser. If you want to see more realistic examples than on the sartoralist then checkout the styleforums thread "what are you wearing today", mentioned elsewhere. Suits work best on someone who is around 5'9". I am quite tall, which means I can look a bit goofy if I wear the wrong things, but just like with being overweight, it is possible to put together a combination that looks good.
Whether a suit looks good for your height just depends on the proportions of the suit compared to your body. A short guy can wear a suit just as well as a tall guy (or vice versa), if he has the right length jacket. This is because the jacket divides the body into two visual sections, the primary effect of which is to either visually shorten or lengthen the legs. Shorter guys look stubby if their jacket is too long and cuts through their thighs.
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.
Modern United States clothing is a thin man's, or woman's, game, but this hasn't always been the case; it doesn't have to be the case that the fat are unfashionable. European clothing as late as the 18th century, and especially in the 15th-16th centuries, was designed for a heavier average weight than the current one (and this is without beginning to discuss, for example, traditional Chinese clothing).
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.
Dress 250 years old and you'll probably look like a tool unless you take up EVERY attribute that was fashionable in that period. Are you going to wear a periwig? Sneakers don't go well with a tricorn hat.
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.
Most people use a fake plastic knife to get around Scottish restrictions on carrying blades.
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.
While it's true most Sartorialist "models" aren't overweight (and that's simply a result of the author's filtering), they aren't especially good looking either. They're just random people who happen to have very good fashion sense. That's the whole point of the blog after all.
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.
I don't think the first guy gets away with the first guy's look, it looks terrible. The trousers are a ghastly colour, texture and shape, the jumper is a different yet still unpleasant colour and a poor fit, the jacket is a nice jacket but a terrible fit, the socks are ugly and the boots don't go with the rest of it. That he is pictured in a sartorial blog is everything that makes me think fashionistas are making it up as they go along while laughing to themselves and pocketing stacks of cash into the bargain.
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.
http://www.thesartorialist.blogspot.com/