I am firmly in the "I don't have enough money to get tired of buying stuff" camp. I mostly buy quality stuff and I am pretty poor, which means that the shopping process takes a lot more time and effort. I wish that I could do the things I want/need to do without buying stuff, but it's difficult, and so I keep buying stuff.
I buy business clothes mostly at Pendleton, some Lands' End and Coldwater Creek (womens clothes only there) as well. Only on sale/clearance, for well under half price. I've been buying running gear from Playmakers, a local activewear/shoe store focused on running. I buy camping gear mostly from REI. I monitor all those stores--the online ones anyway--for clearances and sales, and buy clothes ahead for the next season once they get discounted.
Nah, I'm not running out of fun and interesting ways to spend money. I tend to run out of money long before that point.
And I agree, Brooks Brothers makes some nice stuff. They have an outlet-type store in a mall in metro Detroit and we've found some nice stuff there for good prices, when its clearanced out. Only trouble is their women's clothes only go up to size 12.