Originally Posted by LA Guy
I think that the fact that the suit doesn't look like it just walked out of Bergdorf's is part of it, and the man's, charm. Everyone (with the means) can get a really expensive, very well fitting suit, and it will fit well. Pulling off a cheaper looking suit which doesn't fit magazine ad aesthetics is much cooler, imo.
I have heard this argument before, but I think that it is misapplied in this case. The most common form that I have heard is applied to streetwear (e.g. if you've got money, it's easy to go into a well-curated boutique store - or even American Rag in LA and walk out with an of-the-moment outfit, but doing it with thrift is more legit/challenging). I agree that one could say the same about walking into Jay Kos or Bergdorf and walking out with a perfectly kitted-out look. But I really hesitate to give someone extra points for wearing an inferior garment that doesn't fit well. There are several reasons for this: (i) one can get good garments at great prices, either at sales or via thrift/Ebay; (ii) bad quality/bad aesthetics can be seen (and avoided) even when choosing only among cheaper suits - there are suits at lower prices that will have nicer lapels than his suit; (iii) he may well have paid a lot for that badly-made suit, buying at Etro or Hugo Boss (hey, he's Austrian); (iv) fit issues can be addressed by an alterations tailor, which is in most people's means. So while I can still give the guy credit for nice color combos and creativity in the outfit, I certainly don't see any extra charm in wearing a (visibly) cheaper suit. I would give him points if he were wearing a beautifully-made suit that he got for next to nothing - I am not saying that one should spend a lot to get a look, but when you undercut your look by wearing a not-so-nice suit, I don't find it charming.