There are several things to take into consideration, so here goes:
As fare as tailor made suits go, I agree, they are, by far, the best you can get. Sorting them out is sometimes wearisome though and bear in mind that it can - and will - take six weeks to get them ready
Although these days I too wear primarily bespoke suits, my world opened up when a colleague of mine a couple of years ago introduced me to Italian suits.Not your truly expensive stuff from Borelli, Brioni or Kiton, mind you, but the almost bespoke brands like Boglioli, Rafaelle Caruso and, to a lesser extent in my case because I am smaller and therefore not the type, Corneliani and Zegna
If you are a regular guy with a regular fit any Italian brand or other with Italian fit will make you look like a million dollars.
Since these suits can be bought sometimes below 1200 dollars they make a fantastic investment. You need to consider to buy more than 2 suits because wearing them too often and taking them (only 2 mind you) to the drycleaners too often will make any suit look like it was bought at Walmart after only a year. So I would advice to go for 3 suits at least, one being blue, another grey and a third maybe a small pinstripe (not the big chalks please, they look like jailbars).
Another thing to consider when buying suits is to have them fit tightly. People generally tend to buy one size too large because it fits so comfortably. That looks ridiculous. If you go to a good shop or tailor take your time, actually listen to them even when they want you to try a size smaller than you'd care for.
Also: When you go for the almost-bespoke Italian type suit, make sure that when they fit it to your arms length, they reapply the kissing - and usable! - buttons. This tells other in the know that you either have an expensive - though we know better - Italian suit or that you have a bespoke suit. It is THE signature of a man that takes care of his - obviously expensive since few suits can pull off this trick - clothing
Of course when are able to unbutton your arm partly it also gives more room for your watch to show your good taste in watches too.
Cufflinks and shirts: I agree completely that these should be bespoke and if possible slim fit. Also be sure to be able to wear cufflinks. Nothing looks so silly as a cheap shirt in a great suit. Best shirts? A completely white shirt, naturally. You should have at least 5 of them. As for cuffs: Ken has some great Paul Smith cuffs, cuffs with a twist which are good value cause the store I go toe has them for 3 times that much in store.
Shoes: Lets see. Black and somewhat pointy are popular in higher echelons everywhere. Not so sure in for instance finance about cognac coloured shoes although I personally love my Santoni's. Then again, I work in a major IT corp not in finance.
Since we don't care so much for ties in IT I may not be the best to advice on that, but I have a large collection and the ones I carry most are the plain coloured: Deep red (looks good on every suit, pinstripe or blue or whatever), light blue (on your blue or grey suit) are good choices
Learn to tie a double windsor - not that hard - and you look like a million dollars. James Bond eat your heart out ;-)
Enjoy finding out what you like. And let us know how things went
Rgrds
JG2000