The structured jacket look like it has too much shoulder padding to look good with jeans, as well as too smooth/glossy a fabric. I'd go with the unstructured jacket unless you're concerned about looking too casual at work.
In my experience (I've tapered about a dozen pairs of trousers) if they have a crease, you should be taking an equal amount from both seams, or the crease will be shifted off-center. If they're casual trousers, you're fine reducing the circumference by an inch or so from just a single seam. That said, if you're removing a large amount width across a short amount of length (eg only below the knee), taking in both seams is safer.
I have a pair of these and they're actually 100% wool (and pretty nice), I think they just mixed up the descriptions on the site. Last summer I ordered a "wool blend" Club Monaco sport coat that ended up being 60% wool/40% poly... I returned it. Hopefully Club Monaco is not trying to race Banana Republic to the bottom by sneaking in synthetic fabrics, but I'm not too impressed.
I just got the Sutton "herringbone" and "textured" trousers in the mail and their fabric content is 43% polyester, 36% wool, 17% acrylic and 4% silk (despite the site listing them as "wool"). Is it too much to ask for pants retailing for $200CAD to be all wool? Is there any practical benefit to such a content mix or is it simply cost-cutting?
I picked up a pair of the Sutton "wool melange" trousers and they're very slim but with a higher rise than the old Connor fit. The 100% wool fabric is quite nice as well. My 30x30 pair measures:Waist: 32.5"Front rise: 10.25"Leg opening: 13" Hope that helps.
I'm in Canada as well and have had trouble acquiring AEs at a reasonable price – Harry Rosen carries them but I've never seen them go on sale there. Ordering direct from AE results in a shipping charge of around $40USD, and factoring in whatever customs/duty they apply at the border, it's probably cheaper to get them at HR even if they're on sale from AE.
My advice is to try them on at HR and determine you size, and then find that size on eBay. If anyone other...
I attended their travelling tailor event in Vancouver last year and ended up returning the suit and free shirt - I really wanted to like them, but neither the suit nor shirt fit properly, and the shirt sleeves were shorter than the jacket sleeves even though they were presumably working from a single measurement of my arms... They were really accommodating about the return, though, to their credit.