OK, so here's a description of my journey and findings:
I started in the 40s on Madison Avenue. I went to Paul Stuart to try on the suit I was leaning towards to begin with. It felt nice and was a good fit, right off the rack. Then I went around to check out the shoes. Allen Edmonds looked ok, but felt a little cheap and were not what I was looking for. Alden had decent ones that seemed pretty solidly made, but not much selection. Then I sauntered up to Saks to see what they had. I checked out Zegna and Isaih. They were both reeeeeeallly nice and felt breathable and comfortable when I put them on, almost like slipping on some comfortable slippers after a long day on your feet. However, they were $2800 and $3300 respectively. I wasn't crazy about all of their patterns though. Then I walked over to the Ralph Lauren section and tried on their Polo and Purple Label jackets. They were positively unflattering. The part where the sleeves joined the back stuck way out, and the canvassing felt stiff and awkward. With every suit I tried on, a 40 Regular fit me perfectly, but the RL suits just didn't fit.
Then I went around to check out shoes. I started at Leffot, which everyone seemed to be raving about. The proprietor was cordial, but they had a very limited selection. I was able to check out a few of the brands and compare. I liked some of the Edward Greene a lot, but they were $1200. A day or two later, I walked down Madison, stopping in various shoe stores through the 60s (starting with John Lobb). I can see why everyone says Lobb is the way to go. The Hutton was a bit of a disappointment. I really liked it online, but in reality, the color on display was quite dull. I liked it better in the pewter than in the brown. But all-in-all, I really like the John Lobbs and will be back in June or July when they have their biannual sale. They're quality, and you can tell. Next stop: Crockett & Jones. I stopped in several shoe stores on the way down Madison, (including Barneys) but nothing seemed quite right. So I looked around C&J and could see that they are a nice step up from Alden, but in a vastly different class than Lobbs. I really liked the Westbournes (as suggested by jrd617). The color is warm and inviting, they feel like good quality, and the brouging is sporty but not overdone.
Next, I went back to Paul Stuart to try on the suit I started with, and still liked it. Since I was next door, I went over to Brooks Brothers, which used to be my go to brand until a recent debacle with an OCBD soured my impression of them (plus a feeling over the last 15 years that they're regressing to the mean). Maybe it was this latent hostility that clouded my judgement on their suits, but they all seemed deadly. They were either solid and boring or pinstriped and boring. I wasn't impressed with fit or quality either.
OK, here is with what I will be going:
1) The Paul Stuart Samuelsohn blue birdseye suit ($1484). It felt soft and comfortable, it fit well, and is just above the middle of my price range.
Paul Stuart - Wool Birdseye Suit
2) The Crockett and Jones Westbourne in Chestnut. ($625) Thanks, jrd617. These will be perfect. They also sell them at Paul Stuart for $3 more, so I hope they have my size since C&J didn't.
Crockett & Jones - Westbourne Chestnut Burnished Calf
3) LS Men's Clothing for a shirt (will talk to Izzy). I will timidly begin my adventure into the bespoke territory with some custom shirts. Whether they can do custom or MTM in time is an issue, but i hope so. Otherwise, I'll have them tailor one for me while they make me a few. Going here is based in part on kennethpollock's suggestion.
LS Mens Clothing - Custom Dress Shirts
4) I'll probably get a patterned shirt, so I might be bold and go with a solid tie. I know everyone always has fun mixing patterns (as do I), but the fact that most people go for patterned ties makes it almost more interesting to go with a solid one.
5) A haircut at my usual haunt:
Paul Molé - Mens Haircutters
So, I feel pretty good about this. Thank you all for your help.
Special thanks to Mark Seitelman for setting me in the right direction; doctorman for excellent patience, practicality and positivity—your guidance has been invaluable; and jrd617 for imparting your knowledge and assistance with the shoes. I've gotten great advice here. I knew this was the right place to come. It's great to have so many experts in so many places converge here! To think that 15 years ago, this resource wouldn't have existed is amazing. Thanks so much to all of you.
Edited by John B - 4/30/13 at 4:57pm