Menswear writer. Editor at @putthison. Creator of @RLGoesHard. Bylines at The New York Times, The Financial Times, Politico, Esquire, and Mr. Porter
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Disclosure: I don't know how the patterns were drafted for the clothes featured in this thread. That would make a big difference in how they should be judged. But for the purpose of this thread, I'll assume they're ready-to-wear or designer (i.e., adjusted off a block pattern). 
First, some basics. It's easier to dress like this if you involve some kind of activity. I suggest going out to a nice restaurant or bar. Or going to a party or an evening show. You can also dress like this just to have fun in the city (e.g., going to the museum). 
This will be quite expensive for guys who are into menswear. For instance, Spier & Mackay is popular among guys who are budget-conscious but want quality tailoring. Their $400 suits will now arrive with $100 tax bill. 
First, I should note there's nothing wrong with buying a ~$250 suit (unless it was made in a sweatshop). In fact, you can look great in cheaper suits. Here's @andrewdefrank in a $200 suit vs. Tristan in a $10,000 suit (so he claims). I think Andrew's tailoring looks better. 
Remember the premise: fit guys can look good in any random t-shirt (and presumably any outfit) while fat guys have to rely on "fashion." I argue that, regardless of your build, it helps to know some things about how to dress.
As usual, there are no hard and fast rules on hemming. Everything depends on the aesthetic you're working within. In some aesthetics, it's fine to have a very cropped leg (pic 1). In other aesthetics, it's fine to have a stacked leg (pic 2). Depends on the look! 
First, why is layering useful, aside from potentially protecting you from the elements (e.g., rain, snow, cold, etc)? The main reason is because a lot of outfits look pretty plain without some finishing layer. Most people nowadays wear jeans, chinos, button-ups, and t-shirts. 
It's hard to look good in a polo for all of the same reasons it's hard to look good in just a button-up dress shirt or a t-shirt. The garment typically has no silhouette. Polos are relatively simple garments with straight seams and a short placket. 
Wool and down are just materials, like linen or cotton. They can be used to make anything. Down doesn't have to be a Canada Goose parka. It can be something like a Rocky Mountain Featherbed vest or a Nigel Cabourn Everest parka. 
IMO, Daniel Craig's outfit has too much velvet. Compare him to Hiroyuki Senada, who wears a similar outfit but ditches the vest. I think this improves the look, as black velvet can suck up a lot of light. The white shirt here provides some needed contrast. 
