Go custom fit, wherever it is you choose to buy from. Having a custom fit suit is much nicer than "off the rack" suits (even when altered to fit).
I use a travelling tailor from Hong Kong called Vogue Tailors , they come to Calgary every September and March (clothes arrive 2-3 weeks after the visit) and have a huge selection of fabrics and colors to choose from (they do shirts too) email is: email@example.com
The first appointment will take about 45 mins to do your measurements and take photo's of your posture etc. then pick out colors and fabrics.
There are a few of these companies around, the one I use has a package deal that is $1,100 USD for 2 suits & 4 shirts. This might be overkill for your needs since you have gotten away without a suit for quite a while, but they have pricing per suit/shirt and other packages as well.
My brother in law used them for his wedding suit (and shirt) as well as the groomsmen to have all the suits the same cut and color and so did a few different friends and you can bargain with them for a package like that. You will still need to decide if you and the groomsmen are wearing a vest (and if so, if yours will be any different than theirs), what tie to wear (and maybe pocket square) and what shoes (and socks!). If you go with Vogue, the sales guy "Bhat" will happily recommend color, style, cut, shoes, tie, the works for you to look your best. I imagine other tailors will as well, but base that decision on if you like what the tailor is wearing themselves.
Once you have a suit you might be surprised at the number of occasions that it is useful for.
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