A black-tie Black Friday a few years ago in the shop
First off, great question. This is sort of the perfect time to be thinking about black tie. It's before the rush of holiday events, and gives you a few weeks for alterations if you need to make any tweaks, and a chance to hunt down the bow tie you haven't seen since your last formal event…and it also gives you a chance to get ahead of any unexpected surprises (size, taste, you name it).
I'm a big believer that every guy should own his own tuxedo. It pretty much never goes out of style and one could argue that the best a man ever looks is in a tux. So I'd find an occasion – maybe it's your own wedding, maybe, as in your case, you're just a guest, or maybe it's an award you've won – and invest in looking great that night. This gives a real purpose to the purchase, and as a result you'll forever be prepared for any formal occasion that comes your way. (Or at least for a decade or so.)
Overall, I wanna try to blend in in formal settings, but I always want to have a little flourish… something unexpected… something differentiating without being distracting. And I like to have a few options to play with so I can dial it up or down based on the occasion.
So I have two tuxedos – a black tuxedo with a shawl collar, and a midnight navy tuxedo with peak lapels. (I'm not sure there's many shades of blue that I don't like… but here I want to keep it as close to traditional black as possible. Or as the Italians will call it, blu scuro.) The peak lapel is a bit more traditional – probably what comes to mind when you think 'tuxedo' - whereas the shawl collar one has a bit more flair to it… you may recognize it as what James Bond usually wears (see Dr. No.) (I also have tails. And for the record, I have worn them once.)
I've got 3 shirts and 3 shoes that I mix and match depending on the occasion. For the shirts, I have a pleated front, a pique front, and I have a plain white roxford dress shirt, all with a spread collar and all with single cuffs. (Single cuffs work similarly to a French cuff but are not quite as fussy. There's no fold back.) The easy-going one is the roxford, with Trocas shell buttons. The standard buttons on our shirts are so beautiful that – to me – they are equal to studs. Our tuxedo shirts actually come with button-out plackets so you can swap in studs… which I usually do with both the pique front and the pleated front options.
By the way, I'm not hung up on the idea that studs and cufflinks have to match. I like when they do, and we sell a few "dress sets" for that tight look, but it's not a huge thing. I typically like either sterling silver or unlacquered brass, so they get that natural tarnish to them. I also love cheap and cheerful black or white silk knots in my cuffs as well. What else up top? Black-tie is just about the only time I personally wear a bow tie. Ideally, you want the bow tie material to match the trim, so let your jacket be your guide. A satin bow with a satin lapel, a grosgrain bow with a grosgrain lapel, etc. Mine are silk faille so I'm wearing that one. I usually skip the cummerbund…it tends to add visual girth. (Makes me look fatter.)
Shoes-wise, I've got 3 go-tos - a pair of black calfskin Chelsea boots with a leather sole, black Belgian loafers, and black lace-ups. The black Belgian loafers are typically with no socks (and is usually my summer go-to), the Chelsea boots are a little rock 'n' roll but still totally appropriate, and the lace-ups are going to be more formal or when you're on the fence… they'll never look out of place. This isn't the time for kooky socks, so go for black. Silk is the dressier option, but regular over-the-calf merino wool will work too.
So for YOUR upcoming weddings… if I were in your shoes? I'd say the classic peak-lapel tuxedo in black, the pique front shirt, the silk faille bow tie, black silk knot cufflinks, and because of the seasonality, the black Chelseas. If boots feel too out-there for you, go with some lace-ups and you'll still be one of the best dressed guys in the room. And the beauty of black tie is that you can wear the exact same thing to the next wedding… and the one after that… and so on…
Hope this helps… and have fun!