First off, congrats on your dedication to stepping your game up.
Originally Posted by breadstick
Now, may I suggest a bit of footwear-game-up-stepping, too? Owning a pair of Redwing Gentleman Travellers as I do, I can attest to the quality of their footwear, but ... they are far clunkier than you'd want a good suit-wearing shoe to be. (They'd work for the more casual aspects, but only barely.) Besides, you will need black shoes for that black suit, so you might as well get "real" dress shoes rather than making casual boots try to do too much.
Since you mostly wear other clothing and the suits will be for occasional wear, three should do just fine. May I suggest that instead of black, you go for midnight blue? It's going to be much less common than black (which "everyone" will have), and will be just as good or better for evenings, and much better in daytime. BTW, midnight blue is the "other acceptable" version, besides black, for tuxedos, and it is said to look "blacker than black" under the artificial lights of the evening.
Light grey ... go for it. Get it made in a lighter, summer-appropriate fabric. Prepare for a long, outdoor, July wedding where you will spend a great deal of time baking in the afternoon sun. (Not that you can't wear it hundreds of other times in cooler weather, but ... there's your extreme.)
Instead of the blue or brown suit (both fine choices) may I suggest instead ... a navy blue blazer. (Well, "odd jacket", since I do not recommend the brass buttons.) This will give you a slightly less formal option than another suit ... dress it up with proper dress slacks ... dress it down with chinos or chords ... or jeans if you must ... so that you can tweak your outfit a bit more if the need arises for that flexibility.
I like your "do it once ... right" mentality. Find the tailor in town you want to go with, and (unless he retires or turns out to not do a good job) stick with him. Each MTM suit will be better "for you" than the last, as he tweaks his understanding of what fits you. So, get one suit made at a time, rather than all three.
Consider getting two pairs of pants made for each suit. That's the way it used to be done all the time. Pants wear out faster than jackets, and are the cheapest half of the suit, so ... getting two pair made will roughly double the lifespan of your suit. (No, you can't go back ten years form now and ask him to make another pair of pants to match the suit ... if he's actually still not retired yet ... as it will be virtually impossible to match the "dye batch" of the suit material.
Be there or be square. Only I can do both!
"My lord, I will use them according to their desert."
"God's bodykins, man, much better: use every man
after his desert, and who should 'scape whipping?"
Veteran of the Great Irisch Moos Campaign of 2008-09