I bought a faux shearling coat similar to the TSV last year in purple (without the hood) and find it to be roomy enough for a thick jumper enough, but still looks fitted, if that makes sense. Btw, I'm a size 10 (being called busty would be the understatement of the year)! and bought the XS. Sometimes these oversized coats are so big on me, I could get someone else inside with me with room to spare!
It also fits well on the shoulders and the sleeves are the right length. (I'm fairly broad shouldered and about 5' 7"). It's quite thin, (if it's the same as last year's TSV), so I think you'd still need to layer up in the colder weather. Definitely not warm enough for Chicago in November, unless you wear loads of layers underneath. I've been there a few times at that time of year and a 'sleeping bag' would be about just right for me!
I agree, the sizing is all over the place. I find their leather jackets and raincoats quite snug, but the shearlings more roomy. I also bought one of their suede coats which is more fitted again.
P.S. If it's the same purple as I have, it's a gorgeous colour. I'm very tempted to buy one today, but I'm trying to talk myself out of it. :thinking: