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I'm interested in the 'no khakis' suggestions as well. I think I have subconsciously gone in this direction (for Saturday night), but I've only recently heard such a maxim actually articulated. I was visiting a friend in Manhattan (a banker who still has a job), and when I asked him if my attire was okay (before we went out one evening), he said, "well, you kind of look like a hick: wearing khakis in NY."

I thought some more about it. Although I rarely wear jeans during the week, preferring khakis, I do think that khakis can actually look a little bit too rustic for a night on the town. Sometimes chinos can suggest that you are trying to dress up, but this is the best that you can do. Jeans look nice, without such pretensions, and good wool trousers send the message that you actually know what you're doing. Now, I bemoan the demise of "proper attire" as much as the next forumite, but that doesn't mean that jeans don't look great. There are times, usually at traditionally formal affairs such as an orchestra concert, when I feel like wearing a bow-tie as a big "go to hell" to our casual society, but most of the time, it's better to make one's resistance more subtle: wear quality clothing that fits, with an eye for color and texture. An example: 501s look great over slim ankle boots, under a grey cashmere* sweater, and sport-coats (if the tailoring is slim).

*I've actually relegated most of my cashmere to date duty. I've always been disappointed by its durability, and this has made it difficult for me to be relaxed while wearing cashmere. Nevertheless, it's worth having a few cashmere sweaters, because women can't seem to keep their hands off of it. Maybe they just care more about texture than we do.
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