Hello again! I’ve seen the Tommy Hilfiger trim/slim fit line at Macy’s and I think on sale they’re a pretty good deal. If I already didn’t have my current Lands’ End suits, I’d consider buying them. If you can, try them on in person first to get a better idea of their fit and look on you.
As for waiting, I guess the limiting factor here is how quickly your tailor could turn around alterations. To be on the safe side, I’d venture a guess of four weeks, however, you should call and ask. You’ll probably need the sides taken in, taper on the legs, taking in the seat, maybe a cuff adjustment on both the sleeves, possibly adjusting pant hems. It’ll also probably take you about a week or so to get the suit. So, a theoretical lead time of five weeks. Maybe wait a week or two? Your call though. Also, keep in mind you could buy the Tommy Hilfiger suit now (while it’s on sale) and return it if it doesn’t work out or the Lands’ End suits come on sale within that time frame.
I’d go with a navy knit tie, because I tend to think black is traditionally for funerals. You might also want to consider a wedding tie. For a pocket square, keep it simple with a white linen square with a TV fold.