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I have 6 pair now. 1 pair Indy boots, plus 5 out of my 6 main shoes for work are shell cordovan Aldens:
Plus my C&J Marlowes:
...2 black 2 burgundy 2 brown. That's what I wanted. Still want a pair of Whiskey and a pair of Ravello, though, just 'cause. Also maybe a monk. But I am pretty much set for years on the above.
Polo is made by Corneliani, which is excellent stuff. I don't know where you've been looking, or if you've been looking at non-suiting items, which would be made in China by randoms making 80 cents an hour or something.
Like basically every suit, yeah it's RTW - different cuts look good on different people, Corneliani stuff works for me. With double breasted stuff the main thing is the button stance. I like a high button stance at a reasonable width. I see a lot of DB jackets nowadays (to the extent people are making them) setting the buttons too narrowly. It just creates really odd looking proportions. On the flip side, if the stance is too low (i.e. you show a lot of shirt and have a really long lapel) it just looks dated.
Suitsupply, all those online MTM programs are pretty much trash in terms of workmanship and materials. The only benefit is getting it MTM, and actually getting the measurements right is probably going to take you a few tries. I honestly have way, way better luck sizing RTW in a cut I know I like, and doing a few minor alterations.
Yep, Corneliani has made the suits for a long time now. You have to go back about 15 years to find a Polo suit made elsewhere (until around 2000 they were US-made).
As far as MTM goes, it does all depend on who's dealing with you and also how much feedback you provide to the person. The online services are a huge crapshoot because you just can't do MTM through email. It doesn't work, unless you're willing to fail 4 times before you get something decent. If you can get measured in person and do a fitting, it has a much higher chance of succeeding. Particularly if you can actually recognize what you don't like about the fit and communicate that to the person you're dealing with. Inability to communicate issues (can't spot a problem) or unwillingness (they must know what they're doing so I won't second-guess) are the two biggest reasons that MTM gets screwed up once you're actually there.
I don't know about lucky. There's enough out there that if you look you can find a particular label and cut that works for your frame, generally speaking. Being tall doesn't hurt.