My size 40 in red is 25.5 in the sleeve and 22.5 pit to pit. It seems slightly tighter in the gut and chest than my other TS shirts, but that may just be the thicker fabric. I also haven't washed it yet and wore it for the first time today.
You should probably try a 42.
I love the shirts but really wish they came with spare buttons. I have four shirts that aren't very old, but three of them have lost a button. I have some free replacements on the way from TS, but 75% of my TS shirts are out of service while I wait.
Just a suggestion.
I wouldn't wear the strand with jeans. I think you would get a lot more use out of something like the AE Leeds. Lots of companies make a PTB shoe. If you want new, J Crew probably has a lower quality version for cheap.
Brand new, never worn or tried on. Unlined natural chromexcel beefroll penny loafer.
See details here: http://oakstreetbootmakers.com/footwear/natural-chromexcel-beefroll-penny-loafer
$225 OBO Shipped to CONUS.