This is a too broad question to be answered precisely.
First of all, the concept of "being classy" is highly debated and rather subjective. It is impossible to separate this notion from the fashion trends of any era, so the judgment will always be impaired depending on the taste, the age, the social environment.
Secondly, if you refer to tailoring only, one has to face the dilemma that today in many places the suit is becoming more of a "costume" than a normal piece of clothing. And how is possible to consider a costume to be classy?
However, I want to reply given the following premises: this is my personal viewpoint and I will assume that we are in a world in which wearing a suit outside your own home is natural as not going around naked (or you can pretend to apply this to the micro-environment of a workplace in which everybody wears suits).
Here's the slogan: the classy suit should neither stand out as eccentric, nor be a lifeless industrial piece made to the most boring standards.
Let me elaborate. What I believe one should avoid are the fo1llowing situations:
1) garments made with flashy colours or exaggerated cuts (too skinny, too baggy) even if perfectly fitted to the wearer. This latter circumstance is even worse, since it conveys that the wearer purposely seeks for attention, which is the opposite reason a man should wear a suit for;
2) garments that have absolutely no flair, no interesting features, that could be as trivial as a slight texture in a solid fabric, a nice hourglass shape, wadded sleeveheads, waterfall buttons on sleeves, or subtler characteristics like buttons spaced differently from the mass, lapels shaped in a conservative yet balanced way, trousers not wrinkling when standing because the measurements are respectful of the anatomy...
I could continue endlessly, listing features that in my view are classy or cheesy. Just another example of bad behaviour: working buttons on sleeves that are kept open to show off. This is quite the opposite of good taste: you don't want to stand out in a suit, unless you are a showman or a circus manager.
Finally let me talk about brands. In my opnion, to obtain a classy suit there is no "Gospel brand", namely a label from which you are assured to buy great stuff. In principle, every brand can sell either classy or crappy stuff. I have seen remarkable examples of moderation from Zara suits and ridiculous gaudiness in suits made by Savile Row tailors.
The point is, the lower the price point, the less likely is to find a good fit in some areas; but I would choose a cheap. fused classy suit from Zara and I'd have it altered to my frame instead of a expensive showy, fully canvassed and hand picked suit from Cad&Dandy, just to name one. After all, good alterationst can reallly do miracles, giving to a mass produced garment that bit of individuality.
Finally, I do believe that there are some brands from which it is very difficult to buy a wrong garment. Among these I include Brioni (all the suits I have seen, even those more fashion oriented, were extremely well proportioned and never aggressive or loud), Canali (apart from the catwalk garments, all you see in a Canali boutique is generally very good taste), Corneliani, Caruso (excluding the fashion foward collections), most from Ralph Lauren (some new collections are just laughable), Oxxford (very classy American look), Hackett (usually a good mixture of traditional and modern).
There are many others, of course. But buying blindly from one of these won't give you a classy look. You have to come up what you like by yourself and, most importantly, get the garments fitted from a skilled tailor.
It's kind of an insider-tip in old Germany, because nearly unknown here, in general. I didn't knew the brand, before I got my winter-woolscarf in one of Breuninger's department-stores.
I have to agree with a lot of what Mathematicus says. Specific brands are rather redundant, they can all produce stuff that is horribly gaudy and stuff that is very classy.
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