I agree with most folks that you get better service and attention when dressed up. But there is a fun side to dressing down, at least if you are an elite member.

Sometimes when visiting hot places, I'm dressed way, way down. Yet with my high status at the airlines and hotels I'm guaranteed first class and pre-booked into nice rooms. I love the looks on the people who didn't get upgraded when I waltz into 1st class dressed in rags.

Not that I cultivate this, but in California (nowhere else) there is an image that the more casual you dress, the wealthier you are. I used to work for a guy who was an instant-Internet millionaire. After his first big payday, he started wearing his pajamas to work. He was rich and didn't give a **** what anyone thought about it.