For bespoke I urge you guys to check out Label NYC (www.label.co). They're making a three-piece dark blue mohair suit for my wedding. I'll post some more thoughts and info after my first fitting. I was put up on them by a colleague who swears by their work and service.
I can't speak on...
I always have issues with how shirts fit off the rack, regardless of brand. My suggestion to you (and this is what I do as well) is to buy an inexpensive, decent quality shirt like Charles Tyrwhitt (you can get them for $50 a pop or less) and have them tailored. I like CT because they offer a...
The vest is a zip-in for the jacket and the jacket is Esprit.
You can get something similar from Massimo Dutti:
http://www.massimodutti.com/us/en/men/jackets/quilted/reversible-waistcoat-c1192511p4525545.html?colorId=700...
These are from Boggi -- https://shop.boggi.com/en/prodotto/polacchino-scamosciato-3/
They're ok but I think you can probably find something better at a similar price point. I think Meermin's chukka boots are really nice. I like the shape of these a lot...