If you are basically in a suit environment I would do the following. Find a $1200-$2500 per suit custom suit maker (at least in the U.S.). Have them make up two midprice suits and you will find they offer you great deals on custom shirts to go with them. So, two suits at $1700 each, 6 shirts at $125 or so each and you will still have $1000 left for a good pair of shoes and a few ties. If you are in the U.S. I can steer you to one of these outfits and they actually come to your office. Could it be more convenient? I don't even shop anymore for work clothes.The only downside is that you will end up in ever more expensive suits as we do with watches. The folks who pay $4,000 for a suit have always amazed me. Let's face it, you can get a better true custom "rep" for half the price. And yes, you can even show the suit maker a picture of one you loved in a magazine and voila.