Thanks, taking the time is something I enjoy doing and others have definitely taken their time to answer my questions in regards to stuff sartorial. So, I’m happy to help if I can.
I’m going to break this down into a few parts. First, in regards to having to wear a tuxedo at least once a year, I’m going to recommend you buy one. For about the price of 1-2 rentals, you could’ve bought a full tuxedo, gotten it altered to fit properly, look better and gotten a shirt that also fits nicely.
I wrote about the tuxedo I bought last year and have a guide to buying a tuxedo (dinner suit) on eBay. Read over it and consider investing in a solid piece of formal wear. Occasionally, I’ll post links to tuxedos/dinner suits I find on eBay here as well. The one thing I didn’t touch on and would probably go back and do differently is use an online made-to-measure shirt service to make me a perfect-fitting tuxedo shirt. If you have a MTM service you trust and a good shirt to model your measurements off of, then I’d go that route. It’d probably be about the same price and fit better.
I’m going to tackle the shoe question next. It’s probably not going to look great with a suit. Passable? Maybe. Generally, I’d say loafers are too casual to be worn with a suit and you need some sort of laced-up shoe.
That said, I’m in the camp of suggestion you find a pair of plain, black captoes. They’ll be wearable with your tuxedo and suit at the same time. Not sure what your budget is right now, but Nordstrom has the Allen Edmonds Park Avenues on sale right now for $200. That’s about 38% off retail price. You could also try your luck on eBay to snipe a pair. Speaking of Ferragamo, I actually found my black captoes from them for $50.
And that brings us back to the suit. I’m a fan and wear several Lands’ End suits. The fact you can choose your jackets and trousers (yes, go plain front) separately is a good thing. Navy will work just fine for a color, although I think the dark charcoal is also perfectly fine.
I will say that you’ll definitely want to have your suit altered, unless you luck out with it fitting perfectly. The trousers will probably need to be tapered and taken in at the seat, too.
If you’re set on buying from Lands’ End though, then I would hold off for a bit. Subscribe to their email list and wait for the inevitable 25-30% off all items sales they seem to have every month. If you don’t think you can wait too terribly long, then sign up and wait for a discount code that’ll probably knock at least $50 off your order with free shipping.
In regards to the shirt, I’d go with Brooks Brothers ESF shirts, too. If you only really need one shirt, the only get one. However, if you feel you could use an oxford and another shirt, then go for the 3 for $200 deal. I love their OCBDs.
For a silk grenadine tie, I think Derek’s necktie series at Put This On did a great job with suggestions, but to add my two cents, the Kent Wang grenadine is phenomenal. I just received it today as a birthday gift from my brother and it knots amazingly and looks just great.
Hope this was helpful!