Thanks so much for the feedback fellas, really helpful. I spent another 2 days looking around on the web and B&M stores. I found some Perry Ellis suits that fit well but were polyester blends. I found a few at Sacks but no vests. :(
I went back to Macys.com and think I found a score!
Alfani Red Med Grey Stepweave:
I measure 39 Reg and 33x32 so I ordered a 38R and a 40R jacket. I also ordered 32x34 and 34x34 pants. I figured I would then try them all on and take all the separates to the tailor and go from there. I really hope I liked the fabric and fit as I know you can't really get a 'feel' for a suit over the internet. I am going off of a few reviews that mention Alfani Red as being one of the better budget wool suits. I am more happy with the color as it is more of a true med grey.
I feel like this is my best shot. I will keep looking around while I wait for these pieces to ship.
Due to the quick and helpful replies I can see my self posting my whole outfit shopping experience on here!