Here's my simple solution to the high-end suit fetish amongst my fellow legal professionals - consignment shops. My office and industry culture requires nice suits for men and women. I see some younger members of the profession get the '2 for $199' specials and get mocked for it - it is difficult to pull off successfully, especially over time when those cheapies tend to wear out. There are a few professed Mustachians (who are anything but) who load up when a Hong Kong tailor comes to town and sets up in a hotel for a few days. A few more buy their work clothes while on vacation, justifying their trip to London as 'savings' when they go to Saville Row. Mostly, the folks I work with head downstairs to the high-end clothiers and pull out their Amex. There is a strong self-justification cycle which says that it takes money to make money, and this is simply the price of entry. This is also the same reason I see so many people leasing the entry-model German luxo car they can't actually afford.
Anyway, barring becoming a brilliant iconoclast (the barrister who refuses to wear socks, even in court, comes to mind), my hack is to go to consignment shops. My wife dragged me into one a few years ago searching for a name-brand bag she wanted but would not pay retail for. Lo and behold, they had a small and under-serviced mens section. Looking through I found Zegnas, Canalis, Armanis for under $200. About half were likely from male models (38 tall, 28 waist) but many were from normal downtown guys who likely had to replace their wardrobe each year to keep up with fashions. For under $500 every two years, I still manage to wear $1000 suits to work every day. While my colleagues dress in expensive clothes, most lawyers are honestly nerds (my wife says we're just engineers in better clothes) who don't keep up with fashion that carefully. So quality gets noticed but currency of style does not. Stay conservative and you're fine.
So, I have managed to work in a high-end legal environment, dress the part, and I stay under MMM's $600 annual spend for clothes. I feel badass about it. I am willing to bet there are a few high-end clothes consignment shops in every major city. Be patient and opportunistic and you will luck out.
T.